AU2019371591A1 - (Hetero)arylimidazole compound and harmful organism control agent - Google Patents

Abstract

The present invention addresses the problem of providing a (hetero)arylimidazole compound which has an excellent harmful organism controlling activity, particularly an excellent insecticidal activity and/or an excellent acaricidal activity, also has excellent safety, and can be synthesized industrially advantageously. The (hetero)arylimidazole compound according to the present invention is a compound represented by formula (I), or an N-oxide compound, a stereoisomer, a tautomer or a hydrate of the compound, or a salt of the compound, the N-oxide compound, the stereoisomer, the tautomer or the hydrate. In formula (I), B

Description

DESCRIPTION TITLE OF THE INVENTION (HETERO)ARYLIMIDAZOLE COMPOUND AND HARMFUL ORGANISM CONTROL AGENT

Technical Field

[0001]

The present invention relates to a (hetero)aryl

imidazole compound and a pest control agent. More

specifically, the present invention relates to a

(hetero)aryl imidazole compound that has excellent

insecticidal activity and/or acaricidal activity, is

excellent in safety, and may be industrially

advantageously synthesized, and a pest control agent

containing it as an active ingredient.

The present application claims the priority of

Japanese Patent Application No. 2018-202998 filed on

October 29, 2018, the contents of which are incorporated

herein.

Background Art

[0002]

Various compounds having insecticidal or acaricidal

activity have been proposed. For practical use of such

compounds as agrochemicals, it is required not only to

have sufficiently high efficacy but to be less likely to

cause chemical resistance, to cause neither phytotoxicity

to plants nor soil pollution, and to be low toxic to

livestock, fishes, etc.

[0003] Patent document 1 discloses a compound represented

by the formula (A), etc.

N C1I \ / CF 3

F 3C 5X N (A)

[0004] Patent document 2 discloses a compound represented

by the formula (B), etc.

N\ F3C~i:DCN N(B)

Prior Art Documents

Patent Documents

[0005] Patent document 1: W02017/104741A

Patent document 2: W02016/121997A

Summary of the Invention

Object to be Solved by the Invention

[0006] An object of the present invention is to provide a

(hetero)aryl imidazole compound that is excellent in pest

control activity, particularly, insecticidal activity

and/or acaricidal activity, is excellent in safety, and

may be industrially advantageously synthesized. Another object of the present invention is to provide a pest control agent, an insecticide or acaricide, an ectoparasite control agent, or an endoparasite control agent or expellant containing the (hetero)aryl imidazole compound as an active ingredient. A further object of the present invention is to provide a seed treatment agent, a vegetative propagation organ treatment agent, a granular agrochemical composition for paddy rice seedling nursery box treatment, a soil treatment agent, a bait agent, and a plant growth promoter containing the (hetero)aryl imidazole compound as an active ingredient.

Means to Solve the Object

[0007]

As a result of diligent studies to attain the

objects, the present invention including the following

form has been completed.

[0008]

[1] A compound represented by the formula (I), an N-oxide

compound, stereoisomer, tautomer or hydrate thereof or a

salt of any of these compounds:

R1 N

R N B1 X R2

wherein

B represents a nitrogen atom or CH;

X represents a substituted or unsubstituted C3-8

cycloalkyl group;

R represents a substituted or unsubstituted C1-6

alkylthio group or a substituted or unsubstituted C1-6

alkylsulfonyl group;

R2 represents a substituted or unsubstituted C1-6

alkyl group; and

R represents a substituted or unsubstituted C2-6

alkenyl group.

[0009]

[2] The compound according to the above [1], an N-oxide

compound, stereoisomer, tautomer or hydrate thereof or a

salt of any one of these compounds, wherein the formula

(I) is the formula (II):

R1 N

R4 OH N N X C_ R2 R3()

wherein 1 2 R , R2, and X have the same meanings as described in

the formula (I);

R 3 represents a hydrogen atom or a halogeno group;

R 4 represents a C1-4 haloalkyl group; and

the carbon-carbon double stereo bond represents an E

form or a Z form, or a mixture thereof.

[0010]

[3] A compound represented by any of the formula (III) to

the formula (X), an N-oxide compound, stereoisomer,

tautomer or hydrate thereof or a salt of any of these

compounds:

O=S F N FI F'F F I) 0

C1 HJ( N

F F (IV)

wherein the carbon-carbon double stereo bond represents an

E form or a Z form, or a mixture thereof;

0=s ONS

F H F N N F

F F NVD N F I N _ \ (V) r N F F NOr

N N N

wherein the carbon-carbon double stereo bond represents an

E form or a Z form, or a mixture thereof;

\1/ N N F F F F \N1I FF (VI)

F X N\ O=C

F F N F (X)

[0011]

[4] A pest control agent comprising at least one compound

selected from the group consisting of a compound according

to any one of the above [1] to [3], an N-oxide compound,

stereoisomer, tautomer and hydrate thereof and a salt of

any of these compounds.

[0012]

[5] An insecticide or acaricide comprising at least one

compound selected from the group consisting of a compound

according to any one of the above [1] to [3], an N-oxide

compound, stereoisomer, tautomer and hydrate thereof and a

salt of any of these compounds, as an active ingredient.

[0013]

[6] An ectoparasite control agent comprising at least one

compound selected from the group consisting of a compound

according to any one of the above [1] to [3], an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds, as an active ingredient.

[0014]

[7] An endoparasite control agent or expellant comprising

at least one compound selected from the group consisting

of a compound according to any one of the above [1] to [3],

an N-oxide compound, stereoisomer, tautomer and hydrate

thereof and a salt of any of these compounds, as an active

ingredient.

[0015]

[8] A seed treatment agent or vegetative propagation organ

treatment agent comprising at least one compound selected

from the group consisting of a compound according to any

one of the above [1] to [3], an N-oxide compound,

stereoisomer, tautomer and hydrate thereof and a salt of

any of these compounds, as an active ingredient.

[0016]

[9] A granular agrochemical composition for paddy rice

seedling nursery box treatment comprising at least one

compound selected from the group consisting of a compound

according to any one of the above [1] to [3], an N-oxide

compound, stereoisomer, tautomer and hydrate thereof and a

salt of any of these compounds, as an active ingredient.

[0017]

[10] A soil treatment agent comprising at least one

compound selected from the group consisting of a compound

according to any one of the above [1] to [3], an N-oxide

compound, stereoisomer, tautomer and hydrate thereof and a

salt of any of these compounds, as an active ingredient.

[0018]

[11] A bait agent comprising at least one compound

selected from the group consisting of a compound according

to any one of the above [1] to [31, an N-oxide compound,

stereoisomer, tautomer and hydrate thereof and a salt of

any of these compounds, as an active ingredient.

[0019]

[12] A plant growth promoter comprising at least one

compound selected from the group consisting of a compound

according to any one of the above [1] to [31, an N-oxide

compound, stereoisomer, tautomer and hydrate thereof and a

salt of any of these compounds, as an active ingredient.

Effect of the Invention

[0020]

The (hetero)aryl imidazole compound of the present

invention may control pests that are problems associated

with crops or hygiene. Particularly, the (hetero)aryl

imidazole compound of the present invention may

effectively control agricultural insect pests and acari at

a lower concentration. Furthermore, the (hetero)aryl

imidazole compound of the present invention may

effectively control ectoparasites and endoparasites

harmful to humans and animals.

Also, the (hetero)aryl imidazole compound of the

present invention may be used as a seed treatment agent, a

vegetative propagation organ treatment agent, a granular

agrochemical composition for paddy rice seedling nursery

box treatment, a soil treatment agent, a bait agent, or a

plant growth promoter.

Mode of Carrying Out the Invention

[0021]

[(Hetero)aryl imidazole compound]

The (hetero)aryl imidazole compound of the present invention is a compound represented by the formula (I) (hereinafter, also referred to as compound (I)), an N oxide compound, stereoisomer, tautomer or hydrate thereof

or a salt of any of these compounds. The compound represented by the formula (I) includes every stereoisomer which is an enantiomer or a diastereomer.

R1 N

R N B1 X R (D)

[0022]

In the present invention, the term "unsubstituted" means a group consisting of only a mother nucleus. Only the name of a group consisting of a mother nucleus without the term "substituted" means an "unsubstituted" group

unless otherwise specified. On the other hand, the term "substituted" means that any hydrogen atom of a group consisting of a mother nucleus is substituted with a group (substituent) having a

structure that is the same as or different from that of the mother nucleus. Thus, the "substituent" means another group bonded to the group consisting of a mother nucleus. The number of the substituent may be one or more. Two or

more substituents are the same or different. Terms such as "C1-6" mean that the number of carbon atoms in the group consisting of a mother nucleus is 1 to

6, etc. This number of carbon atoms does not include the

number of carbon atoms present in the substituent. For

example, a butyl group having an ethoxy group as a

substituent is classified into a C2 alkoxy C4 alkyl group.

[0023]

The "substituent" is not particularly limited as

long as the substituent is chemically acceptable and

produces the effect of the present invention. Hereinafter,

a group capable of serving as the "substituent" is

exemplified:

a C1-6 alkyl group such as a methyl group, an ethyl

group, a n-propyl group, an i-propyl group, a n-butyl

group, a s-butyl group, an i-butyl group, a t-butyl group,

a n-pentyl group, and a n-hexyl group;

a C2-6 alkenyl group such as a vinyl group, a 1

propenyl group, a 2-propenyl group (allyl group), a 1

butenyl group, a 2-butenyl group, a 3-butenyl group, a 1

methyl-2-propenyl group, and a 2-methyl-2-propenyl group;

a C2-6 alkynyl group such as an ethynyl group, a 1

propynyl group, a 2-propynyl group, a 1-butynyl group, a

2-butynyl group, a 3-butynyl group, and a 1-methyl-2

propynyl group;

[0024]

a C3-8 cycloalkyl group such as a cyclopropyl group,

a cyclobutyl group, a cyclopentyl group, a cyclohexyl

group, and a cubanyl group;

a C6-10 aryl group such as a phenyl group and a

naphthyl group;

a C6-10 aryl C1-6 alkyl group such as a benzyl group

and a phenethyl group; a 3- to 6-membered heterocyclyl group; a 3- to 6-membered heterocyclyl C1-6 alkyl group;

[0025]

a hydroxy group;

a C1-6 alkoxy group such as a methoxy group, an

ethoxy group, a n-propoxy group, an i-propoxy group, a n

butoxy group, a s-butoxy group, an i-butoxy group, and a

t-butoxy group;

a C2-6 alkenyloxy group such as a vinyloxy group, an

allyloxy group, a propenyloxy group, and a butenyloxy

group;

a C2-6 alkynyloxy group such as an ethynyloxy group

and a propargyloxy group;

a C6-10 aryloxy group such as a phenoxy group and a

naphthoxy group;

a C6-10 aryl C1-6 alkoxy group such as a benzyloxy

group and a phenethyloxy group;

a 5- or 6-membered heteroaryloxy group such as a

thiazolyloxy group and a pyridyloxy group;

a 5- or 6-membered heteroaryl C1-6 alkyloxy group

such as a thiazolylmethyloxy group and a pyridylmethyloxy

group;

[0026]

a formyl group;

a C1-6 alkylcarbonyl group such as an acetyl group

and a propionyl group;

a formyloxy group;

a C1-6 alkylcarbonyloxy group such as an acetyloxy

group and a propionyloxy group;

a C6-10 arylcarbonyl group such as a benzoyl group; a C1-6 alkoxycarbonyl group such as a methoxycarbonyl group, an ethoxycarbonyl group, a n propoxycarbonyl group, an i-propoxycarbonyl group, a n butoxycarbonyl group, and a t-butoxycarbonyl group; a C1-6 alkoxycarbonyloxy group such as a methoxycarbonyloxy group, an ethoxycarbonyloxy group, a n propoxycarbonyloxy group, an i-propoxycarbonyloxy group, a n-butoxycarbonyloxy group, and a t-butoxycarbonyloxy group; a carboxy group;

[0027]

a halogeno group such as a fluoro group, a chloro

group, a bromo group, and an iodo group;

a C1-6 haloalkyl group such as a fluoromethyl group,

a difluoromethyl group, a trifluoromethyl group, a 2,2,2

trifluoroethyl group, a pentafluoroethyl group, a 3,3,3

trifluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group,

a perfluoropropyl group, a 2,2,2-trifluoro-1

trifluoromethylethyl group, a perfluoroisopropyl group, a

4-fluorobutyl group, a 2,2,3,3,4,4,4-heptafluorobutyl

group, a perfluorobutyl group, a perfluoropentyl group, a

perfluorohexyl group, a chloromethyl group, a bromomethyl

group, a dichloromethyl group, a dibromomethyl group, a

trichloromethyl group, a tribromomethyl group, a 1

chloroethyl group, a 2,2,2-trichloroethyl group, a 4

chlorobutyl group, a perchlorohexyl group, and a 2,4,6

trichlorohexyl group;

a C2-6 haloalkenyl group such as a 2-chloro-1

propenyl group and a 2-fluoro-1-butenyl group; a C2-6 haloalkynyl group such as a 4,4-dichloro-1 butynyl group, a 4-fluoro-1-pentynyl group, and a 5-bromo

2-pentynyl group;

a C1-6 haloalkoxy group such as a trifluoromethoxy

group, a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy

group, and a perfluoropropoxy group;

a C2-6 haloalkenyloxy group such as a 2

chloropropenyloxy group and a 3-bromobutenyloxy group;

a C1-6 haloalkylcarbonyl group such as a

chloroacetyl group, a trifluoroacetyl group, and a

trichloroacetyl group;

[0028]

an amino group;

a C1-6 alkyl-substituted amino group such as a

methylamino group, a dimethylamino group, and a

diethylamino group;

a C6-10 arylamino group such as an anilino group and

a naphthylamino group;

a C6-10 aryl C1-6 alkylamino group such as a

benzylamino group and a phenethylamino group;

a formylamino group;

a C1-6 alkylcarbonylamino group such as an

acetylamino group, a propanoylamino group, a butyrylamino

group, and an i-propylcarbonylamino group;

a C1-6 alkoxycarbonylamino group such as a

methoxycarbonylamino group, an ethoxycarbonylamino group,

a n-propoxycarbonylamino group, and an i

propoxycarbonylamino group;

an unsubstituted or substituted aminocarbonyl group

such as an aminocarbonyl group, a dimethylaminocarbonyl group, a phenylaminocarbonyl group, and a N-phenyl-N methylaminocarbonyl group; an imino C1-6 alkyl group such as an iminomethyl group, a (1-imino)ethyl group, and a (1-imino)-n-propyl group; a substituted or unsubstituted N-hydroxyimino C1-6 alkyl group such as a N-hydroxy-iminomethyl group, a (1

(N-hydroxy)-imino)ethyl group, a (1-(N-hydroxy)

imino)propyl group, a N-methoxy-iminomethyl group, and a

(1-(N-methoxy)-imino)ethyl group;

a C1-6 alkoxyimino group such as a methoxyimino

group, an ethoxyimino group, a n-propoxyimino group, an i

propoxyimino group, and a n-butoxyimino group;

an aminocarbonyloxy group;

a C1-6 alkyl-substituted aminocarbonyloxy group such

as an ethylaminocarbonyloxy group and a

dimethylaminocarbonyloxy group;

[0029]

a mercapto group;

a C1-6 alkylthio group such as a methylthio group,

an ethylthio group, a n-propylthio group, an i-propylthio

group, a n-butylthio group, an i-butylthio group, a s

butylthio group, and a t-butylthio group;

a C1-6 haloalkylthio group such as a

trifluoromethylthio group and a 2,2,2-trifluoroethylthio

group;

a C6-10 arylthio group such as a phenylthio group

and a naphthylthio group;

a 5- or 6-membered heteroarylthio group such as a

thiazolylthio group and a pyridylthio group;

[00301 a C1-6 alkylsulfinyl group such as a methylsulfinyl

group, an ethylsulfinyl group, and a t-butylsulfinyl

group;

a C1-6 haloalkylsulfinyl group such as a

trifluoromethylsulfinyl group and a 2,2,2

trifluoroethylsulfinyl group;

a C6-10 arylsulfinyl group such as a phenylsulfinyl

group;

a 5- or 6-membered heteroarylsulfinyl group such as

a thiazolylsulfinyl group and a pyridylsulfinyl group;

[0031]

a C1-6 alkylsulfonyl group such as a methylsulfonyl

group, an ethylsulfonyl group, and a t-butylsulfonyl

group;

a C1-6 haloalkylsulfonyl group such as a

trifluoromethylsulfonyl group and a 2,2,2

trifluoroethylsulfonyl group;

a C6-10 arylsulfonyl group such as a phenylsulfonyl

group;

a 5- or 6-membered heteroarylsulfonyl group such as

a thiazolylsulfonyl group and a pyridylsulfonyl group;

a C1-6 alkylsulfonyloxy group such as a

methylsulfonyloxy group, an ethylsulfonyloxy group, and a

t-butylsulfonyloxy group;

a C1-6 haloalkylsulfonyloxy group such as a

trifluoromethylsulfonyloxy group and a 2,2,2

trifluoroethylsulfonyloxy group;

and an aminothiocarbonyl group;

[0032] a tri-C1-6 alkyl-substituted silyl group such as a trimethylsilyl group, a triethylsilyl group, and a t butyldimethylsilyl group; a tri-C6-10 aryl-substituted silyl group such as a triphenylsilyl group; a cyano group; and a nitro group.

[00331

For these "substituents", any hydrogen atom in each

substituent may be substituted with a group having a

distinct structure. In this case, as the "substituent", a

C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy

group, a C1-6 haloalkoxy group, a halogeno group, a cyano

group, a nitro group or the like may be exemplified.

[0034]

The "3- to 6-membered heterocyclyl group" described

above contains 1 to 4 heteroatoms selected from the group

consisting of a nitrogen atom, an oxygen atom and a sulfur

atom as ring-constituting atoms. The heterocyclyl group

may be either monocyclic or polycyclic. The polycyclic

heterocyclyl group has at least one hetero ring, and the

remaining ring(s) may be any of a saturated alicyclic ring,

an unsaturated alicyclic ring and an aromatic ring. As

the "3- to 6-membered heterocyclyl group", a 3- to 6

membered saturated heterocyclyl group, a 5- or 6-membered

heteroaryl group, a 5- or 6-membered partially unsaturated

heterocyclyl group or the like may be exemplified.

[00351

As the 3- to 6-membered saturated heterocyclyl group,

an aziridinyl group, an epoxy group, a pyrrolidinyl group,

a tetrahydrofuranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, a dioxanyl group or the like may be exemplified.

[0036] As the 5-membered heteroaryl group, a pyrrolyl group,

a furyl group, a thienyl group, an imidazolyl group, a

pyrazolyl group, an oxazolyl group, an isoxazolyl group, a

thiazolyl group, an isothiazolyl group, a triazolyl group,

an oxadiazolyl group, a thiadiazolyl group, a tetrazolyl

group or the like may be exemplified.

As the 6-membered heteroaryl group, a pyridyl group,

a pyrazinyl group, a pyrimidinyl group, a pyridazinyl

group, a triazinyl group or the like may be exemplified.

[0037]

[B']

In the formula (I), B represents a nitrogen atom or

CH.

Specifically, the compound represented by the

formula (I) is a compound represented by the following

formula (I-1) or formula (1-2).

[0038]

R1 N

R N(X R21

R1 N

R N N X R (1-2)

In the formula (I-1) and the formula (1-2), X, R1, R2

and R have the same meanings as described in the formula

(I).

[0039] B' is preferably a nitrogen atom.

[0040]

[X]

In the formula (I), X represents a substituted or

unsubstituted C3-8 cycloalkyl group.

[0041]

As the "C3-8 cycloalkyl group" in X, a cyclopropyl

group, a cyclobutyl group, a cyclopentyl group, a

cyclohexyl group, a cubanyl group or the like may be

exemplified.

[0042]

As the "substituted C3-8 cycloalkyl group" in X, a

1-methylcyclopropyl group, a 1-cyanocyclopropyl group, a

1-aminocarbonylcyclopropyl group, a 1

aminothiocarbonylcyclopropyl group, a 1-(pyridin-2

yl)cyclopropyl group or the like may be exemplified.

[0043]

As the substituent on the "C3-8 cycloalkyl group" in

X, a cyano group; an aminocarbonyl group; an

aminothiocarbonyl group; a C1-6 alkyl group such as a

methyl group, an ethyl group, a n-propyl group, an i propyl group, a n-butyl group, a s-butyl group, an i-butyl group, a t-butyl group, a n-pentyl group, and a n-hexyl group; and a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group may be preferably exemplified.

[0044] X is preferably a substituted or unsubstituted

cyclopropyl group, and more preferably an unsubstituted

cyclopropyl group.

[0045]

[R']

In the formula (I), R1 represents a substituted or

unsubstituted C1-6 alkylthio group or a substituted or

unsubstituted C1-6 alkylsulfonyl group.

[0046]

As the "C1-6 alkylthio group" in R', a methylthio

group, an ethylthio group, a n-propylthio group, an i

propylthio group, a n-butylthio group, an i-butylthio

group, a s-butylthio group, a t-butylthio group or the

like may be exemplified.

[0047]

As the "C1-6 alkylsulfonyl group" in R', a

methylsulfonyl group, an ethylsulfonyl group, a t

butylsulfonyl group or the like may be exemplified.

[0048]

As the substituents on the "C1-6 alkylthio group"

and the "C1-6 alkylsulfonyl group" in R', a halogeno group

such as a fluoro group, a chloro group, a bromo group, and

an iodo group may be preferably exemplified.

[0049]

R' is preferably a C1-6 alkylsulfonyl group, and

more preferably an ethylsulfonyl group.

[00501

[R2

In the formula (I), R2 represents a substituted or

unsubstituted C1-6 alkyl group.

[0051]

The "C1-6 alkyl group" in R2 may be linear or

branched. As the "C1-6 alkyl group", a methyl group, an

ethyl group, a n-propyl group, a n-butyl group, a n-pentyl

group, a n-hexyl group, an i-propyl group, an i-butyl

group, a s-butyl group, a t-butyl group, an i-pentyl group,

a neopentyl group, a 2-methylbutyl group, an i-hexyl group

or the like may be exemplified.

[0052]

As the substituent on the "C1-6 alkyl group" in R2

a halogeno group such as a fluoro group, a chloro group, a

bromo group, and an iodo group may be preferably

exemplified.

[00531 R2 is preferably an unsubstituted C1-6 alkyl group,

and more preferably a methyl group.

[0054]

[R]

In the formula (I), R represents a substituted or

unsubstituted C2-6 alkenyl group.

[00551 As the "C2-6 alkenyl group" in R, a vinyl group, a

1-propenyl group, a 2-propenyl group, a 1-butenyl group, a

2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl

group, a 2-methyl-2-propenyl group, a 1-pentenyl group, a

2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group,

a 1-methyl-2-butenyl group, a 2-methyl-2-butenyl group, a

1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a

4-hexenyl group, a 5-hexenyl group or the like may be

exemplified.

[00561 As the "substituted C2-6 alkenyl group" in R, a C2-6

haloalkenyl group such as a 2-fluoro-2-bromovinyl group, a

2,2-dichlorovinyl group, a 2-chloro-2-iodovinyl group, a

2-chloro-1-propenyl group, a 2,3,3,3-tetrafluoro-1

propenyl group, a 3,3,3-trifluoro-1-propenyl group, a 2

chloro-3,3,3-trifluoro-1-propenyl group, a 2-bromo-3,3,3

trifluoro-1-propenyl group, a 3,3,3-trifluoro-2

trifluoromethyl-1-propenyl group, a 2-fluoro-1-butenyl

group, a 3,3,4,4,4-pentafluoro-1-butenyl group, a

2,3,3,4,4,4-hexafluoro-1-butenyl group, a 2-chloro

3,3,4,4,4-pentafluoro-1-butenyl group, a 3,3,4,4,5,5,5

heptafluoro-1-pentenyl group, a 2-chloro-3,3,4,4,5,5,5

heptafluoro-1-pentenyl group, a 2,3,3,4,4,5,5,5

octafluoro-1-pentenyl group, and a 3,3,4,4,5,5,6,6,6

nonafluoro-1-hexenyl group; and a C1-6 haloalkoxy C2-6

haloalkenyl group such as a 1,2-difluoro-2

trifluoromethoxyvinyl group and a 1,2-difluoro-2

perfluoropropoxyvinyl group may be exemplified.

[0057]

As the substituent on the "C2-6 alkenyl group" in R,

a halogeno group such as a fluoro group, a chloro group, a

bromo group, and an iodo group; and a C1-6 haloalkoxy group such as a trifluoromethoxy group, a 2-chloro-n propoxy group, a 2,3-dichlorobutoxy group, and a perfluoropropoxy group may be preferably exemplified.

[0058] R is preferably a C2-6 haloalkenyl group.

[0059] The salt of the compound (I) is not particularly

limited as long as the salt is agriculturally or

horticulturally acceptable. As the salt of the compound

(I), for example, a salt of an inorganic acid such as

hydrochloric acid and sulfuric acid; a salt of an organic

acid such as acetic acid and lactic acid; a salt of an

alkali metal such as lithium, sodium and potassium; a salt

of an alkaline earth metal such as calcium and magnesium;

a salt of a transition metal such as iron and copper; a

salt of an organic base such as ammonia, triethylamine,

tributylamine, pyridine, and hydrazine, or the like may be

exemplified.

[0060]

[Compound represented by formula (II)]

The compound represented by the formula (I) is

preferably a compound represented by the formula (II).

R1

N R4 N X YRCCH R3 (H)3 In the formula (II), 1 2 R , R2, and X have the same meanings as described in

the formula (I).

R 3 represents a hydrogen atom or a halogeno group.

R 4 represents a C1-4 haloalkyl group.

In the formula (II), the carbon-carbon double stereo

bond represents an E form or a Z form, or a mixture

thereof.

[0061]

[R3]

As the "halogeno group" in R , a fluoro group, a chloro group, a bromo group, an iodo group or the like may

be exemplified.

[0062]

[R4]

As the "C1-4 haloalkyl group" in R 4, a fluoromethyl

group, a difluoromethyl group, a trifluoromethyl group, a

2,2,2-trifluoroethyl group, a pentafluoroethyl group, a

3,3,3-trifluoropropyl group, a 2,2,3,3,3-pentafluoropropyl

group, a perfluoropropyl group, a 2,2,2-trifluoro-1

trifluoromethylethyl group, a perfluoroisopropyl group, a

4-fluorobutyl group, a 2,2,3,3,4,4,4-heptafluorobutyl

group, a perfluorobutyl group, a chloromethyl group, a

bromomethyl group, a dichloromethyl group, a dibromomethyl

group, a trichloromethyl group, a tribromomethyl group, a

1-chloroethyl group, a 2,2,2-trichloroethyl group, a 4

chlorobutyl group or the like may be exemplified.

[0063] R4 is preferably a C1-4 fluoroalkyl group such as a

fluoromethyl group, a difluoromethyl group, a

trifluoromethyl group, a 2,2,2-trifluoroethyl group, a

pentafluoroethyl group, a 3,3,3-trifluoropropyl group, a

2,2,3,3,3-pentafluoropropyl group, a perfluoropropyl group,

a 2,2,2-trifluoro-1-trifluoromethylethyl group, a perfluoroisopropyl group, a 4-fluorobutyl group, a

2,2, 3, 3,4,4, 4-heptafluorobutyl group, or a perfluorobutyl

group.

[0064]

The compound represented by the formula (I) is

preferably any of the following compounds.

FF N F N N F F (V)

0 0=::s N

N N

FCr

wherein the carbon-carbon double stereo bond represents an

E form or a Z form, or a mixture thereof.

F (V)

F F Mv

0\ r

F H' F '' N N F NOI C

FhIF /

wherein the carbon-carbon double stereo bond represents an

E F'F form or a Z NC form, or a mixture thereof

. O NN N (V FFI ) FN F F F F F N(X

[0065]

[Production method] The (hetero) aryl imidazole compound of the present invention is not particularly limited by its production method. For example, the (hetero) aryl imidazole compound of the present invention may be obtained by known

production methods described in Examples, etc. Alternatively, the N-oxide compound, salt, or the like of

the compound (I) may be obtained by a known approach from the compound (I).

[0066]

The (hetero)aryl imidazole compound of the present

invention may be produced by, for example, methods given

below.

[0067]

(Synthetic method 1)

R' ~ R'C01 3 N R

Zn CI l 2 K X R t N N X R H R2

wherein X, R' and R2 have the same meanings as described

above; and R represents a Cl-4 fluoroalkyl group such as

a fluoromethyl group, a difluoromethyl group, a

trifluoromethyl group, a 2,2,2-trifluoroethyl group, a

pentafluoroethyl group, a 3,3,3-trifluoropropyl group, a

2,2,3,3,3-pentafluoropropyl group, a perfluoropropyl group,

a 2,2,2-trifluoro-l-trifluoromethylethyl group, a

perfluoroisopropyl group, a 4-fluorobutyl group, a

2,2,3,3,4,4,4-heptafluorobutyl group, or a perfluorobutyl

group.

[0068]

(Synthetic method 2)

1. Et02 CJOR')2

Ni 3 OAC N Zn(R') 2DMPU 2 R i Q N- X H R2 R2 R82

1 2 wherein X, R, R and R have the same meanings as

described above; and R 5 represents a C1-6 alkyl group.

[0069]

(Synthetic method 3)

1,~ CI

R' zzK S PO(OEt} Rl Rl 2. BuSnH Zn(R2DMPU 2 c c

h1 R2 R2

wherein X, R , R2 and R have the same meanings as

described above.

[0070]

(Synthetic method 4)

Rl Rl

H2 - 1) RfCHCABr IMg N, 2)Flurinetng Agents Rt

wherein X, R" R 2 and R have the same meanings as described

above.

[0071]

(Synthetic method 5)

R R Rl N CBrF, PPh F ( Zn(Rf)2DMPU 2 F X

H F R

1 2f wherein X, R, R and R have the same meanings as

described above.

[0072]

(Synthetic method 6)

R1 R1 R x -e. F Zn FX

0 \ N x

H W ~ oi2 h wherein X, R , R2 and R have the same meanings as described above.

[0073]

(Synthetic method 7)

Ri R1 R1 C.CI CN 7 C1)reductin i N Chorinaion

NX IjN ) xZaetl R Cation R 2 2 R2R

RI vinylation R

R2

wherein X, R , R2 and R have the same meanings as

described above.

[0074]

(Synthetic method 8)

0 1 Ri R1 PN R1 C-R' N N C C vinylation R X I-N N x R N N x Rft , N N X R2 R2 R2 12 2

wherein X, R , R2 and R have the same meanings as

described above.

[0075]

(Synthetic method 9)

RI CI R

S N- XH Heck Re action Rf X R2 R 1 2f wherein X, R, R and R have the same meanings as

described above.

[0076]

[Control effect on pest]

The (hetero)aryl imidazole compound of the present

invention is excellent in control effect on pests such as

various agricultural insect pests and acari affecting the

growth of plants.

Also, the (hetero)aryl imidazole compound of the

present invention is a highly safe substance because of

less phytotoxicity to crops and low toxicity to fishes and

warm-blooded animals. Hence, the (hetero)aryl imidazole

compound of the present invention is useful as an active

ingredient for insecticides or acaricides.

Furthermore, in recent years, many insect pests such

as diamondback moth, white-backed plant hopper, leafhopper,

and aphid have developed resistance to various existing

chemicals, causing problems of insufficient efficacy of

these chemicals. Thus, chemicals effective for insect

pests of resistant strains have been desired. The

(hetero)aryl imidazole compound of the present invention

exhibits an excellent control effect not only on sensitive

strains but also on insect pests of various resistant

strains and even acari of acaricide-resistant strains.

[0077]

The (hetero)aryl imidazole compound of the present

invention is excellent in control effect on ectoparasites

and endoparasites harmful to humans and animals. Also,

the (hetero)aryl imidazole compound of the present

invention is a highly safe substance because of low

toxicity to fishes and warm-blooded animals. Hence, the

(hetero)aryl imidazole compound of the present invention

is useful as an active ingredient for ectoparasite and

endoparasite control agents.

[0078]

The (hetero)aryl imidazole compound of the present

invention exhibits efficacy at every developmental stage

of organisms to be controlled, and exhibits an excellent control effect on, for example, eggs, nymphs, larvae, pupae, and adults of acari, insects, and the like.

[0079]

[Pest control agent]

The pest control agent of the present invention

contains at least one active ingredient selected from the

(hetero)aryl imidazole compounds of the present invention.

The amount of the (hetero)aryl imidazole compound

contained in the pest control agent of the present

invention is not particularly limited as long as its pest

control effect is exhibited. The pest control agent is an

agent controlling pests and includes an insecticide or

acaricide, an ectoparasite control agent, or an

endoparasite control agent or expellant, or the like.

[0080]

The pest control agent of the present invention may

be used as a mixture or in combination with another active

ingredient such as a fungicide, an insecticide or

acaricide, a nematicide, or a pesticide for soil insect

pests; a plant regulating agent, a synergist, a fertilizer,

a soil improvement agent, animal feed, or the like.

The combination of the (hetero)aryl imidazole

compound of the present invention with another active

ingredient may be expected to have synergistic effects on

insecticidal, acaricidal, or nematicidal activity. The

synergistic effects may be confirmed by the equation of

Colby (Colby. S.R.; Calculating Synergistic and

Antagonistic Responses of Herbicide Combinations; Weeds 15,

p. 20-22, 1967) according to a standard method.

[0081]

Specific examples of the insecticide or acaricide,

the nematicide, the pesticide for soil insect pests, the

anthelmintic agent, and the like that may be used as a

mixture or in combination with the pest control agent of

the present invention will be shown below.

[0082]

(1) Acetylcholinesterase inhibitors:

(a) carbamate-based: alanycarb, aldicarb, bendiocarb,

benfuracarb, butocarboxim, butoxycarboxim, carbaryl,

carbofuran, carbosulfan, ethiofencarb, fenobucarb,

formetanate, furathiocarb, isoprocarb, methiocarb,

methomyl, oxamyl, pirimicarb, propoxur, thiodicarb,

thiofanox, triazamate, trimethacarb, XMC, xylylcarb,

fenothiocarb, MIPC, MPMC, MTMC, aldoxycarb, allyxycarb,

aminocarb, bufencarb, chloethocarb, metam sodium, and

promecarb;

[00831 (b) organophosphorus-based: acephate, azamethiphos,

azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos,

chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos

methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon,

dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos,

disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos,

fenitrothion, fenthion, fosthiazate, heptenophos,

imicyafos, isofenphos, isocarbophos, isoxathion, malathion,

mecarbam, methamidophos, methidathion, mevinphos,

monocrotophos, naled, omethoate, oxydemeton-methyl,

parathion, parathion-methyl, phenthoate, phorate,

phosalone, phosmet, phosphamidon, phoxim, pirimiphos

methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion, bromophos-ethyl, BRP, carbophenothion, cyanofenphos, CYAP, demeton-S-methyl sulfone, dialifos, dichlofenthion, dioxabenzofos, etrimfos, fensulfothion, flupyrazofos, fonofos, formothion, fosmethilan, isazofos, iodofenphos, methacrifos, pirimiphos-ethyl, phosphocarb, propaphos, prothoate, and sulprofos.

[0084]

(2) GABAergic chloride ion channel antagonists: acetoprole,

chlordene, endosulfan, ethiprole, fipronil, pyrafluprole,

pyriprole, camphechlor, heptachlor, and dienochlor.

(3) Sodium channel modulators: acrinathrin, d-cis-trans

allethrin, d-trans allethrin, bifenthrin, bioallethrin,

bioallethrin S-cyclopentyl isomers, bioresmethrin,

cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin,

lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin,

alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin,

zeta-cypermethrin, cyphenothrin [(1R)-trans isomers],

deltamethrin, empenthrin [(EZ)-(1R)-isomers],

esfenvalerate, etofenprox, fenpropathrin, fenvalerate,

flucythrinate, flumethrin, tau-fluvalinate, halfenprox,

imiprothrin, kadethrin, permethrin, phenothrin [(1R)-trans

isomers], prallethrin, pyrethrum, resmethrin, silafluofen,

tefluthrin, tetramethrin [(1R)-isomers], tralomethrin,

transfluthrin, allethrin, pyrethrin, pyrethrin I,

pyrethrin II, profluthrin, dimefluthrin, bioethanomethrin,

biopermethrin, transpermethrin, fenfluthrin, fenpirithrin, flubrocythrinate, flufenprox, metofluthrin, protrifenbute, pyresmethrin, and terallethrin.

[00851

(4) Nicotinic acetylcholine receptor agonists: acetamiprid,

clothianidin, dinotefuran, imidacloprid, nitenpyram,

nithiazine, thiacloprid, thiamethoxam, sulfoxaflor,

nicotine, flupyradifurone, and flupyrimin.

(5) Nicotinic acetylcholine receptor allosteric

modulators: spinetoram and spinosad.

(6) Chloride channel activators: abamectin, emamectin

benzoate, lepimectin, milbemectin, ivermectin, selamectin,

doramectin, eprinomectin, moxidectin, milbemycin,

milbemycin oxime, and nemadectin.

(7) Juvenile hormone-like substances: hydroprene,

kinoprene, methoprene, fenoxycarb, pyriproxyfen,

diofenolan, epofenonane, and triprene.

(8) Other nonspecific inhibitors: methyl bromide,

chloropicrin, sulfuryl fluoride, borax, and tartar emetic.

(9) Homoptera selective feeding inhibitors: flonicamid,

pymetrozine, and pyrifluquinazon.

[00861 (10) Mite growth inhibitors: clofentezine, diflovidazin,

hexythiazox, and etoxazole.

(11) Insect midgut inner membrane disrupting agents

derived from microorganisms: Bacillus thuringiensis subsp.

Isuraerenshi, Bacillus sphaericus, Bacillus thuringiensis

subsp. Aizawai, Bacillus thuringiensis subsp. Kurstaki,

Bacillus thuringiensis subsp. Tenebrionis, and Bt crop

proteins: CrylAb, CrylAc, CrylFa, CrylA.105, Cry2Ab, Vip3A,

mCry3A, Cry3Ab, Cry3Bb, and Cry34Abl/Cry35Abl.

(12) Mitochondrial ATP biosynthetic enzyme inhibitors:

diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide,

propargite, and tetradifon.

(13) Oxidative phosphorylation uncouplers: chlorfenapyr,

sulfluramid, DNOC, binapacryl, dinobuton, and dinocap.

(14) Nicotinic acetylcholine receptor channel blockers:

bensultap, cartap hydrochloride, nereistoxin, thiosultap

sodium, and thiocyclam.

(15) Chitin synthesis inhibitors: bistrifluron,

chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron,

hexaflumuron, lufenuron, novaluron, noviflumuron,

teflubenzuron, triflumuron, buprofezin, and fluazuron.

(16) Diptera molting disrupting agents: cyromazine.

(17) Molting hormone receptor agonists: chromafenozide,

halofenozide, methoxyfenozide, and tebufenozide.

(18) Octopamine receptor agonists: amitraz, demiditraz,

and chlordimeform.

(19) Mitochondrial electron transport system complex III

inhibitors: acequinocyl, fluacrypyrim, and hydramethylnon.

(20) Mitochondrial electron transport system complex I

inhibitors: fenazaquin, fenpyroximate, pyrimidifen,

pyridaben, tebufenpyrad, tolfenpyrad, and rotenone.

[0087]

(21) Voltage-gated sodium channel blockers: indoxacarb and

metaflumizone.

(22) Acetyl CoA carboxylase inhibitors: spirodiclofen,

spiromesifen, and spirotetramat.

(23) Mitochondrial electron transport system complex IV

inhibitors: aluminum phosphide, calcium phosphide,

phosphine, zinc phosphide, and cyanide.

(24) Mitochondrial electron transport system complex II

inhibitors: cyenopyrafen, cyflumetofen, and pyflubumide.

(25) Ryanodine receptor modulators: chlorantraniliprole,

cyantraniliprole, flubendiamide, cyclaniliprole, and

tetraniliprole.

(26) Mixed function oxidase inhibitor compounds: piperonyl

butoxide.

(27) Latrophilin receptor agonists: depsipeptide, cyclic

depsipeptide, 24-membered cyclic depsipeptide, and

emodepside.

(28) Other agents (based on an unknown mechanism of

action): azadirachtin, benzoximate, bifenazate,

bromopropylate, chinomethionate, cryolite, dicofol,

pyridalyl, benclothiaz, sulfur, amidoflumet, 1,3

dichloropropene, DCIP, phenisobromolate, benzomate,

metaldehyde, chlorobenzilate, clothiazoben, dicyclanil,

fenoxacrim, fentrifanil, flubenzimin, fluphenazine,

gossyplure, japonilure, metoxadiazone, petroleum,

potassium oleate, tetrasul, triarathene, afidopyropen,

flometoquin, flufiprole, fluensulfone, meperfluthrin,

tetramethylfluthrin, tralopyril, dimefluthrin,

methylneodecanamide, fluralaner, afoxolaner, fluxametamide,

-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5

dihydroisoxazol-3-yl]-2-(1H-1,2,4-triazol-1

yl)benzonitrile (CAS: 943137-49-3), broflanilide, and

other m-diamides.

[00881

(29) Anthelmintic agents:

(a) benzimidazole-based: fenbendazole, albendazole,

triclabendazole, oxibendazole, mebendazole, oxfendazole, parbendazole, flubendazole, febantel, netobimin, thiophanate, thiabendazole, and cambendazole;

(b) salicylanilide-based: closantel, oxyclozanide,

rafoxanide, and niclosamide;

(c) substituted phenol-based: nitroxinil and nitroscanate;

(d) pyrimidine-based: pyrantel and morantel;

(e) imidazothiazole-based: levamisole and tetramisole;

(f) tetrahydropyrimidine-based: praziquantel and

epsiprantel;

(g) other anthelmintic agents: cyclodiene, ryania,

clorsulon, metronidazole, demiditraz, piperazine,

diethylcarbamazine, dichlorophene, monepantel,

tribendimidine, amidantel, thiacetarsamide, melarsomine,

and arsenamide.

[00891 Specific examples of the fungicide that may be used

as a mixture or in combination with the pest control agent

of the present invention will be shown below.

(1) Nucleic acid biosynthesis inhibitors:

(a) RNA polymerase I inhibitors: benalaxyl, benalaxyl-M,

furalaxyl, metalaxyl, metalaxyl-M, oxadixyl, clozylacon,

and ofurace;

(b) adenosine deaminase inhibitors: bupirimate,

dimethirimol, and ethirimol;

(c) DNA/RNA synthesis inhibitors: hymexazol and

octhilinone;

(d) DNA topoisomerase II inhibitors: oxolinic acid.

[00901 (2) Mitotic inhibitors and cell division inhibitors:

(a) B-tubulin polymerization inhibitors: benomyl,

carbendazim, chlorfenazole, fuberidazole, thiabendazole,

thiophanate, thiophanate-methyl, diethofencarb, zoxamide,

and ethaboxam;

(b) cell division inhibitors: pencycuron;

(c) spectrin-like protein delocalization inhibitors:

fluopicolide.

[0091]

(3) Respiration inhibitors:

(a) complex I NADH oxidation-reduction enzyme inhibitors:

diflumetorim and tolfenpyrad;

(b) complex II succinate dehydrogenase inhibitors:

benodanil, flutolanil, mepronil, isofetamid, fluopyram,

fenfuram, furmecyclox, carboxin, oxycarboxin, thifluzamide,

benzovindiflupyr, bixafen, fluxapyroxad, furametpyr,

isopyrazam, penflufen, penthiopyrad, sedaxane, and

boscalid;

(c) complex III ubiquinol oxidase Qo inhibitors:

azoxystrobin, coumoxystrobin, coumethoxystrobin,

enoxastrobin, flufenoxystrobin, picoxystrobin,

pyraoxystrobin, pyraclostrobin, pyrametostrobin,

triclopyricarb, kresoxim-methyl, trifloxystrobin,

dimoxystrobin, fenaminstrobin, metominostrobin,

orysastrobin, famoxadone, fluoxastrobin, fenamidone, and

pyribencarb;

(d) complex III ubiquinol reductase Qi inhibitors:

cyazofamid and amisulbrom;

(e) oxidative phosphorylation uncoupling agents:

binapacryl, meptyldinocap, dinocap, fluazinam, and

ferimzone;

(f) oxidative phosphorylation inhibitors (ATP synthase

inhibitors): fentin acetate, fentin chloride, and fentin

hydroxide;

(g) ATP production inhibitors: silthiofam;

(h) complex III: Qx (unknown) inhibitor of cytochrome bcl

(ubiquinone reductase): ametoctradin.

[0092]

(4) Amino acid and protein synthesis inhibitors

(a) methionine biosynthesis inhibitors: andoprim,

cyprodinil, mepanipyrim, and pyrimethanil;

(b) protein synthesis inhibitors: blasticidin-S,

kasugamycin, kasugamycin hydrochloride, streptomycin, and

oxytetracycline.

[00931 (5) Signal transduction inhibitors:

(a) signal transduction inhibitors: quinoxyfen and

proquinazid;

(b) MAP/histidine kinase inhibitors in osmotic signal

transduction: fenpiclonil, fludioxonil, chlozolinate,

iprodione, procymidone, and vinclozolin.

[0094]

(6) Lipid and cell membrane synthesis inhibitors:

(a) phospholipid biosynthesis, methyltransferase

inhibitors: edifenphos, iprobenfos, pyrazophos, and

isoprothiolane;

(b) lipid peroxidation agents: biphenyl, chloroneb,

dicloran, quintozene, tecnazene, tolclofos-methyl, and

etridiazole;

(c) agents that act on cell membranes: iodocarb,

propamocarb, propamocarb hydrochloride, propamocarb

fosetylate, and prothiocarb;

(d) microorganisms that disrupt cell membranes of

pathogens: Bacillus subtilis bacteria, Bacillus subtilis

QST713 strain, Bacillus subtilis FZB24 strain, Bacillus

subtilis MBI600 strain, and Bacillus subtilis D747 strain;

(e) agents that disrupt cell membranes: extracts of

Melaleuca alternifolia (tea tree).

[00951 (7) Cell membrane sterol biosynthesis inhibitors:

(a) C14-demethylation inhibitors in sterol biosynthesis:

triforine, pyrifenox, pyrisoxazole, fenarimol,

flurprimidol, nuarimol, imazalil, imazalil sulfate,

oxpoconazole, pefurazoate, prochloraz, triflumizole,

viniconazole, azaconazole, bitertanol, bromuconazole,

cyproconazole, diclobutrazol, difenoconazole, diniconazole,

diniconazole-M, epoxiconazole, etaconazole, fenbuconazole,

fluquinconazole, flusilazole, flutriafol, fluconazole,

fluconazole-cis, hexaconazole, imibenconazole, ipconazole,

metconazole, myclobutanil, penconazole, propiconazole,

quinconazole, simeconazole, tebuconazole, tetraconazole,

triadimefon, triadimenol, triticonazole, prothioconazole,

and voriconazole;

(b) A14 reductase and sterol A8 - A7-isomerase inhibitors

in sterol biosynthesis: aldimorph, dodemorph, dodemorph

acetate, fenpropimorph, tridemorph, fenpropidin, piperalin,

and spiroxamine;

(c) 3-keto reductase inhibitors in C4-demethylation in the

sterol biosynthesis system: fenhexamid and fenpyrazamine;

(d) squalene epoxidase inhibitors in the sterol

biosynthesis system: pyributicarb, naftifine, and

terbinafine.

[00961 (8) Cell wall synthesis inhibitors

(a) trehalase inhibitors: validamycin;

(b) chitin synthase inhibitors: polyoxin and polyoxorim;

(c) cellulose synthase inhibitors: dimethomorph, flumorph,

pyrimorph, benthiavalicarb, iprovalicarb, tolprocarb,

valifenalate, and mandipropamid.

[0097]

(9) Melanin biosynthesis inhibitors

(a) melanin biosynthesis reductase inhibitors: fthalide,

pyroquilon, and tricyclazole;

(b) melanin biosynthesis anhydrase inhibitors: carpropamid,

diclocymet, and fenoxanil;

[00981 (10) Host plant resistance inducers:

(a) agents that act on salicylic acid synthesis pathway:

acibenzolar-S-methyl;

(b) others: probenazole, tiadinil, isotianil, laminarin,

and giant knotweed extracts.

[00991 (11) Agents with unknown mode of action: cymoxanil,

fosetyl aluminum, phosphoric acid (phosphate), tecloftalam,

triazoxide, flusulfamide, diclomezine, methasulfocarb,

cyflufenamid, metrafenone, pyriofenone, dodine, dodine

free base, and flutianil.

[0100]

(12) Agents having multiple active sites: copper (copper

salt), Bordeaux mixture, copper hydroxide, copper

naphthalate, copper oxide, copper oxychloride, copper

sulfate, sulfur, sulfur products, calcium polysulfide,

ferbam, mancozeb, maneb, mancopper, metiram, polycarbamate,

propineb, thiram, zineb, ziram, captan, captafol, folpet,

chlorothalonil, dichlofluanid, tolylfluanid, guazatine,

iminoctadine triacetate, iminoctadine trialbesilate,

anilazine, dithianon, chinomethionate, and fluoroimide.

[0101]

(13) Other agents: DBEDC, fluoro folpet, guazatine acetate,

bis(8-quinolinolato)copper(II), propamidine, chloropicrin,

cyprofuram, agrobacterium, bethoxazin, diphenylamine,

methyl isothiocyanate (MITC), mildiomycin, capsaicin,

cufraneb, cyprosulfamide, dazomet, debacarb, dichlorophene,

difenzoquat, difenzoquat methyl sulfonate, flumetover,

fosetyl calcium, fosetyl sodium, irumamycin, natamycin,

nitrothal-isopropyl, oxamocarb, propanosine sodium,

pyrrolnitrin, tebufloquin, tolnifanide, zarilamid,

algophase, amicarthiazol, oxathiapiprolin, metiram zinc,

benthiazole, trichlamide, uniconazole, oxyfenthiin, and

picarbutrazox.

[0102]

Specific examples of the plant regulating agent that

may be used as a mixture or in combination with the pest

control agent of the present invention will be shown below.

Abscisic acid, kinetin, benzylaminopurine, 1,3

diphenylurea, forchlorfenuron, thidiazuron, chlorfenuron,

dihydrozeatin, gibberellin A, gibberellin A4, gibberellin

A7, gibberellin A3, 1-methylcyclopropane, N acetylaminoethoxyvinylglycine (also called aviglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA,

4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid,

dichlorprop, phenothiol, 1-naphthyl acetamide,

ethychlozate, cloxyfonac, maleic acid hydrazide, 2,3,5

triiodobenzoic acid, salicylic acid, methyl salicylate,

(-)-jasmonic acid, methyl jasmonate, (+)-strigol, (+)

deoxystrigol, (+)-orobanchol, (+)-sorgolactone, 4-oxo-4

(2-phenylethyl)aminobutyric acid, ethephon, chlormequat,

mepiquat chloride, benzyl adenine, and 5-aminolevulinic

acid.

[0103]

[Insecticide or acaricide]

The insecticide or acaricide of the present

invention contains at least one active ingredient selected

from the (hetero)aryl imidazole compounds of the present

invention. The amount of the (hetero)aryl imidazole

compound contained in the insecticide or acaricide of the

present invention is not particularly limited as long as

its insecticidal or acaricidal effect is exhibited.

[0104]

The insecticide or acaricide of the present

invention is preferably used for plants such as cereals;

vegetables; root vegetables; tubers and roots; flowers and

ornamental plants; fruit trees; ornamental foliage plants

and trees of tea, coffee, cacao, and the like; feed crops;

lawn grasses; and cotton.

In the application to plants, the pest control agent

or the insecticide or acaricide of the present invention

may be used for any site such as a leaf, a stem, a stalk, a flower, a bud, a fruit, a seed, a sprout, a root, a tuber, a tuberous root, a shoot, or a slip.

The insecticide or acaricide of the present

invention is not particularly limited by the species of

the plant to which the pest control agent or the

insecticide or acaricide is applied. As the plant species,

for example, an original species, a variant species, an

improved variety, a cultivar, a mutant, a hybrid, a

genetically modified organism (GMO) or the like may be

exemplified.

[0105]

The insecticide or acaricide of the present

invention may be used in seed treatment, foliage

application, soil application, submerged application, or

the like in order to control various agricultural insect

pests and acari.

[0106]

Specific examples of various agricultural insect

pests and acari controllable with the insecticide or

acaricide of the present invention will be shown below.

[0107]

(1) Butterflies or moths of the order Lepidoptera

(a) moths of the family Arctiidae, for example, Hyphantria

cunea and Lemyra imparilis;

(b) moths of the family Bucculatricidae, for example,

Bucculatrix pyrivorella;

(c) moths of the family Carposinidae, for example,

Carposina sasakii;

(d) moths of the family Crambidae, for example, Diaphania

indica and Diaphania nitidalis of Diaphania spp.; for example, Ostrinia furnacalis, Ostrinia nubilalis, and

Ostrinia scapulalis of Ostrinia spp.; and Chilo

suppressalis, Cnaphalocrocis medinalis, Conogethes

punctiferalis, Diatraea grandiosella, Glyphodes pyloalis,

Hellula undalis, and Parapediasia teterrella;

(e) moths of the family Gelechiidae, for example,

Helcystogramma triannulella, Pectinophora gossypiella,

Phthorimaea operculella, and Sitotroga cerealella;

(f) moths of the family Geometridae, for example, Ascotis

selenaria;

(g) moths of the family Gracillariidae, for example,

Caloptilia theivora, Phyllocnistis citrella, and

Phyllonorycter ringoniella;

(h) butterflies of the family Hesperiidae, for example,

Parnara guttata;

(i) moths of the family Lasiocampidae, for example,

Malacosoma neustria;

(j) moths of the family Lymantriidae, for example,

Lymantria dispar and Lymantria monacha of Lymantria spp.;

and Euproctis pseudoconspersa and Orgyia thyellina;

[0108]

(k) moths of the family Lyonetiidae, for example, Lyonetia

clerkella and Lyonetia prunifoliella malinella of Lyonetia

spp.; (1) moths of the family Noctuidae, for example, Spodoptera

depravata, Spodoptera eridania, Spodoptera exigua,

Spodoptera frugiperda, Spodoptera littoralis, and

Spodoptera litura of Spodoptera spp.; for example,

Autographa gamma and Autographa nigrisigna of Autographa

spp.; for example, Agrotis ipsilon and Agrotis segetum of

Agrotis spp.; for example, Helicoverpa armigera,

Helicoverpa assulta, and Helicoverpa zea of Helicoverpa

spp.; for example, Heliothis armigera and Heliothis

virescens of Heliothis spp.; and Aedia leucomelas,

Ctenoplusia agnata, Eudocima tyrannus, Mamestra brassicae,

Mythimna separata, Naranga aenescens, Panolis japonica,

Peridroma saucia, Pseudoplusia includens, and Trichoplusia

ni;

(m) moths of the family Nolidae, for example, Earias

insulana;

(n) butterflies of the family Pieridae, for example,

Pieris brassicae and Pieris rapae crucivora of Pieris

spp.; (o) moths of the family Plutellidae, for example,

Acrolepiopsis sapporensis and Acrolepiopsis suzukiella of

Acrolepiopsis spp.; and Plutella xylostella;

(p) moths of the family Pyralidae, for example, Cadra

cautella, Elasmopalpus lignosellus, Etiella zinckenella,

and Galleria mellonella;

(q) moths of the family Sphingidae, for example, Manduca

quinquemaculata and Manduca sexta of Manduca spp.;

[0109]

(r) moths of the family Stathmopodidae, for example,

Stathmopoda masinissa;

(s) moths of the family Tineidae, for example, Tinea

translucens;

(t) moths of the family Tortricidae, for example,

Adoxophyes honmai and Adoxophyes orana of Adoxophyes spp.;

for example, Archips breviplicanus and Archips

fuscocupreanus of Archips spp.; and Choristoneura fumiferana, Cydia pomonella, Eupoecilia ambiguella, Grapholitha molesta, Homona magnanima, Leguminivora glycinivorella, Lobesia botrana, Matsumuraeses phaseoli, Pandemis heparana, and Sparganothis pilleriana; (u) moths of the family Yponomeutidae, for example,

Argyresthia conjugella.

[0110]

(2) Insect pests of the order Thysanoptera (a) insect pests of the family Phlaeothripidae, for

example, Ponticulothrips diospyrosi; (b) insect pests of the family Thripidae, for example, Frankliniella intonsa and Frankliniella occidentalis of Frankliniella spp.; for example, Thrips palmi and Thrips

tabaci of Thrips spp.; and Heliothrips haemorrhoidalis and Scirtothrips dorsalis.

[0111] (3) Insect pests of the order Hemiptera

(A) the suborder Archaeorrhyncha (a) insect pests of the family Delphacidae, for example, Laodelphax striatella, Nilaparvata lugens, Perkinsiella saccharicida, and Sogatella furcifera.

[0112]

(B) the suborder Clypeorrhyncha (a) insect pests of the family Cicadellidae, for example, Empoasca fabae, Empoasca nipponica, Empoasca onukii, and

Empoasca sakaii of Empoasca spp.; and Arboridia apicalis, Balclutha saltuella, Epiacanthus stramineus, Macrosteles striifrons, and Nephotettix cinctinceps.

[0113]

(C) the suborder Heteroptera

(a) insect pests of the family Alydidae, for example,

Riptortus clavatus;

(b) insect pests of the family Coreidae, for example,

Cletus punctiger and Leptocorisa chinensis;

(c) insect pests of the family Lygaeidae, for example,

Blissus leucopterus, Cavelerius saccharivorus, and Togo

hemipterus;

(d) insect pests of the family Miridae, for example,

Halticus insularis, Lygus lineolaris, Psuedatomoscelis

seriatus, Stenodema sibiricum, Stenotus rubrovittatus, and

Trigonotylus caelestialium;

[0114]

(e) insect pests of the family Pentatomidae, for example,

Nezara antennata and Nezara viridula of Nezara spp.; for

example, Eysarcoris aeneus, Eysarcoris lewisi, and

Eysarcoris ventralis of Eysarcoris spp.; and Dolycoris

baccarum, Eurydema rugosum, Glaucias subpunctatus,

Halyomorpha halys, Piezodorus hybneri, Plautia crossota,

and Scotinophora lurida;

(f) insect pests of the family Pyrrhocoridae, for example,

Dysdercus cingulatus;

(g) insect pests of the family Rhopalidae, for example,

Rhopalus msculatus;

(h) insect pests of the family Scutelleridae, for example,

Eurygaster integriceps;

(i) insect pests of the family Tingidae, for example,

Stephanitis nashi.

[0115]

(D) the suborder Sternorrhyncha

(a) insect pests of the family Adelgidae, for example,

Adelges laricis;

(b) insect pests of the family Aleyrodidae, for example,

Bemisia argentifolii and Bemisia tabaci of Bemisia spp.;

and Aleurocanthus spiniferus, Dialeurodes citri, and

Trialeurodes vaporariorum;

(c) insect pests of the family Aphididae, for example,

Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis

gossypii, Aphis pomi, Aphis sambuci, and Aphis spiraecola

of Aphis spp.; for example, Rhopalosiphum maidis and

Rhopalosiphum padi of Rhopalosiphum spp.; for example,

Dysaphis plantaginea and Dysaphis radicola of Dysaphis

spp.; for example, Macrosiphum avenae and Macrosiphum

euphorbiae of Macrosiphum spp.; for example, Myzus cerasi,

Myzus persicae, and Myzus varians of Myzus spp.; and

Acyrthosiphon pisum, Aulacorthum solani, Brachycaudus

helichrysi, Brevicoryne brassicae, Chaetosiphon

fragaefolii, Hyalopterus pruni, Hyperomyzus lactucae,

Lipaphis erysimi, Megoura viciae, Metopolophium dirhodum,

Nasonovia ribis-nigri, Phorodon humuli, Schizaphis

graminum, Sitobion avenae, and Toxoptera aurantii;

[0116]

(d) insect pests of the family Coccidae, for example,

Ceroplastes ceriferus and Ceroplastes rubens of

Ceroplastes spp.;

(e) insect pests of the family Diaspididae,

Pseudaulacaspis pentagona and Pseudaulacaspis prunicola of

Pseudaulacaspis spp.; for example, Unaspis euonymi and

Unaspis yanonensis of Unaspis spp.; and Aonidiella aurantii, Comstockaspis perniciosa, Fiorinia theae, and

Pseudaonidia paeoniae;

(f) insect pests of the family Margarodidae, for example,

Drosicha corpulenta and Icerya purchasi;

(g) insect pests of the family Phylloxeridae, for example,

Viteus vitifolii;

(h) insect pests of the family Pseudococcidae, for example,

Planococcus citri and Planococcus kuraunhiae of

Planococcus spp.; and Phenacoccus solani and Pseudococcus

comstocki;

(i) insect pests of the family Psyllidae, for example,

Psylla mali and Psylla pyrisuga of Psylla spp.; and

Diaphorina citri.

[0117]

(4) Insect pests of the suborder Polyphaga

(a) insect pests of the family Anobiidae, for example,

Lasioderma serricorne;

(b) insect pests of the family Attelabidae, for example,

Byctiscus betulae and Rhynchites heros;

(c) insect pests of the family Bostrichidae, for example,

Lyctus brunneus;

(d) insect pests of the family Brentidae, for example,

Cylas formicarius;

(e) insect pests of the family Buprestidae, for example,

Agrilus sinuatus;

(f) insect pests of the family Cerambycidae, for example,

Anoplophora malasiaca, Monochamus alternatus, Psacothea

hilaris, and Xylotrechus pyrrhoderus;

(g) insect pests of the family Chrysomelidae, for example,

Bruchus pisorum and Bruchus rufimanus of Bruchus spp.; for example, Diabrotica barberi, Diabrotica undecimpunctata, and Diabrotica virgifera of Diabrotica spp.; for example,

Phyllotreta nemorum and Phyllotreta striolata of

Phyllotreta spp.; and Aulacophora femoralis,

Callosobruchus chinensis, Cassida nebulosa, Chaetocnema

concinna, Leptinotarsa decemlineata, Oulema oryzae, and

Psylliodes angusticollis;

[0118]

(h) insect pests of the family Coccinellidae, for example,

Epilachna varivestis and Epilachna vigintioctopunctata of

Epilachna spp.;

(i) insect pests of the family Curculionidae, for example,

Anthonomus grandis and Anthonomus pomorum of Anthonomus

spp.; for example, Sitophilus granarius and Sitophilus

zeamais of Sitophilus spp.; and Echinocnemus squameus,

Euscepes postfasciatus, Hylobius abietis, Hypera postica,

Lissohoptrus oryzophilus, Otiorhynchus sulcatus, Sitona

lineatus, and Sphenophorus venatus;

(j) insect pests of the family Elateridae, for example,

Melanotus fortnumi and Melanotus tamsuyensis of Melanotus

spp.; (k) insect pests of the family Nitidulidae, for example,

Epuraea domina;

(1) insect pests of the family Scarabaeidae, for example,

Anomala cuprea and Anomala rufocuprea of Anomala spp.; and

Cetonia aurata, Gametis jucunda, Heptophylla picea,

Melolontha melolontha, and Popillia japonica;

(m) insect pests of the family Scolytidae, for example,

Ips typographus;

(n) insect pests of the family Staphylinidae, for example,

Paederus fuscipes;

(o) insect pests of the family Tenebrionidae, for example,

Tenebrio molitor and Tribolium castaneum;

(p) insect pests of the family Trogossitidae, for example,

Tenebroides mauritanicus.

[0119]

(5) Insect pests of the order Diptera

(A) the suborder Brachycera

(a) insect pests of the family Agromyzidae, for example,

Liriomyza bryoniae, Liriomyza chinensis, Liriomyza sativae,

and Liriomyza trifolii of Liriomyza spp.; and Chromatomyia

horticola and Agromyza oryzae;

(b) insect pests of the family Anthomyiidae, for example,

Delia platura and Delia radicum of Delia spp.; and Pegomya

cunicularia;

(c) insect pests of the family Drosophilidae, for example,

Drosophila melanogaster and Drosophila suzukii of

Drosophila spp.;

(d) insect pests of the family Ephydridae, for example,

Hydrellia griseola;

(e) insect pests of the family Psilidae, for example,

Psila rosae;

(f) insect pests of the family Tephritidae, for example,

Bactrocera cucurbitae and Bactrocera dorsalis of

Bactrocera spp.; for example, Rhagoletis cerasi and

Rhagoletis pomonella of Rhagoletis spp.; and Ceratitis

capitata and Dacus oleae.

[0120]

(B) the suborder Nematocera

(a) insect pests of the family Cecidomyiidae, for example,

Asphondylia yushimai, Contarinia sorghicola, Mayetiola

destructor, and Sitodiplosis mosellana.

[0121]

(6) Insect pests of the order Orthoptera

(a) insect pests of the family Acrididae, for example,

Schistocerca americana and Schistocerca gregaria of

Schistocerca spp.; and Chortoicetes terminifera,

Dociostaurus maroccanus, Locusta migratoria, Locustana

pardalina, Nomadacris septemfasciata, and Oxya yezoensis;

(b) insect pests of the family Gryllidae, for example,

Acheta domestica and Teleogryllus emma;

(c) insect pests of the family Gryllotalpidae, for example,

Gryllotalpa orientalis;

(d) insect pests of the family Tettigoniidae, for example,

Tachycines asynamorus.

[0122]

(7) Acari

(A) Acaridida of the order Astigmata

(a) acari of the family Acaridae, for example,

Rhizoglyphus echinopus and Rhizoglyphus robini of

Rhizoglyphus spp.; for example, Tyrophagus neiswanderi,

Tyrophagus perniciosus, Tyrophagus putrescentiae, and

Tyrophagus similis of Tyrophagus spp.; and Acarus siro,

Aleuroglyphus ovatus, and Mycetoglyphus fungivorus;

[0123]

(B) Actinedida of the order Prostigmata

(a) acari of the family Tetranychidae, for example,

Bryobia praetiosa and Bryobia rubrioculus of Bryobia spp.;

for example, Eotetranychus asiaticus, Eotetranychus boreus,

Eotetranychus celtis, Eotetranychus geniculatus,

Eotetranychus kankitus, Eotetranychus pruni, Eotetranychus

shii, Eotetranychus smithi, Eotetranychus suginamensis,

and Eotetranychus uncatus of Eotetranychus spp.; for

example, Oligonychus hondoensis, Oligonychus ilicis,

Oligonychus karamatus, Oligonychus mangiferus, Oligonychus

orthius, Oligonychus perseae, Oligonychus pustulosus,

Oligonychus shinkajii, and Oligonychus ununguis of

Oligonychus spp.; for example, Panonychus citri,

Panonychus mori, and Panonychus ulmi of Panonychus spp.;

for example, Tetranychus cinnabarinus, Tetranychus

kanzawai, Tetranychus ludeni, Tetranychus quercivorus,

Tetranychus phaselus, Tetranychus urticae, Tetranychus

viennensis, and Tetranychus evansi of Tetranychus spp.;

for example, Aponychus corpuzae and Aponychus firmianae of

Aponychus spp.; for example, Sasanychus akitanus and

Sasanychus pusillus of Sasanychus spp.; for example,

Schizotetranychus celarius, Schizotetranychus longus,

Schizotetranychus miscanthi, Schizotetranychus recki, and

Schizotetranychus schizopus of Schizotetranychus spp.; and

Tetranychina harti, Tuckerella pavoniformis, and

Yezonychus sapporensis;

[0124]

(b) acari of the family Tenuipalpidae, for example,

Brevipalpus lewisi, Brevipalpus obovatus, Brevipalpus

phoenicis, Brevipalpus russulus, and Brevipalpus

californicus of Brevipalpus spp.; for example, Tenuipalpus

pacificus and Tenuipalpus zhizhilashviliae of Tenuipalpus

spp.; and Dolichotetranychus floridanus;

(c) acari of the family Eriophyidae, for example, Aceria

diospyri, Aceria ficus, Aceria japonica, Aceria kuko,

Aceria paradianthi, Aceria tiyingi, Aceria tulipae, and

Aceria zoysiea of Aceria spp.; for example, Eriophyes

chibaensis and Eriophyes emarginatae of Eriophyes spp.;

for example, Aculops lycopersici and Aculops pelekassi of

Aculops spp.; for example, Aculus fockeui and Aculus

schlechtendali of Aculus spp.; and Acaphylla theavagrans,

Calacarus carinatus, Colomerus vitis, Calepitrimerus vitis,

Epitrimerus pyri, Paraphytoptus kikus, Paracalacarus

podocarpi, and Phyllocotruta citri;

(d) acari of the family Tarsonemidae, for example,

Tarsonemus bilobatus and Tarsonemus waitei of Tarsonemus

spp.; and Phytonemus pallidus and Polyphagotarsonemus

latus;

(e) acari of the family Penthaleidae, for example,

Penthaleus erythrocephalus and Penthaleus major of

Penthaleus spp.

[0125]

[Ectoparasite control agent]

The ectoparasite control agent of the present

invention contains at least one active ingredient selected

from the (hetero)aryl imidazole compounds of the present

invention. The amount of the (hetero)aryl imidazole

compound contained in the ectoparasite control agent of

the present invention is not particularly limited as long

as its ectoparasite control effect is exhibited.

[0126]

As the host animal to be treated with the

ectoparasite control agent of the present invention, a warm-blooded animal such as a human and a livestock mammal

(e.g., a cow, a horse, a pig, sheep, and a goat), a

laboratory animal (e.g., a mouse, a rat, and a sand rat),

a pet animal (e.g., a hamster, a guinea pig, a dog, a cat,

a horse, a squirrel, a rabbit, and a ferret), wild and zoo

mammals (e.g., a monkey, a fox, a deer, and a buffalo), a

fowl (e.g., a turkey, a duck, a chicken, a quail, and a

goose), and a pet bird (e.g., a pigeon, a parrot, a myna

bird, a Java sparrow, a parakeet, a Bengalese finch, and a

canary bird); and fishes such as salmon, trout, and carp

may be exemplified. In addition, a bee, a stag beetle and

a beetle may be exemplified.

[0127]

The ectoparasite control agent of the present

invention may be applied by a known veterinary approach

(local, oral, parenteral or subcutaneous administration).

As the method therefor, a method of orally administering

tablets, capsules, feed or the like containing the

ectoparasite control agent to animals; a method of

administering the ectoparasite control agent through

dipping liquids, suppositories, injection (intramuscular,

subcutaneous, intravenous, or intraperitoneal injection,

etc.) or the like to animals; a method of locally

administering oily or aqueous liquid formulations by

spraying, pour-on, spot-on or the like; and a method of

kneading the ectoparasite control agent into a resin,

shaping the kneaded product into a suitable shape such as

a collar or an ear tag, and attaching it to animals for

local administration; or the like may be exemplified.

[0128]

Ectoparasites parasitize the inside or the body

surface of host animals, particularly, warm-blooded

animals. Specifically, the ectoparasites parasitize the

backs, armpits, lower abdomens, inner thighs, or the like

of host animals and live by obtaining nutrients such as

blood or dandruff from the animals. As the ectoparasite,

acari, lice, fleas, a mosquito, a stable fly, a flesh fly

or the like may be exemplified. Specific examples of the

ectoparasite controllable with the ectoparasite control

agent of the present invention will be shown below.

[0129]

(1) Acari

acari of the family Dermanyssidae, acari of the family

Macronyssidae, acari of the family Laelapidae, acari of

the family Varroidae, acari of the family Argasidae, acari

of the family Ixodidae, acari of the family Psoroptidae,

acari of the family Sarcoptidae, acari of the family

Knemidokoptidae, acari of the family Demodixidae, acari of

the family Trombiculidae, and insect parasitic acari such

as acari of the family Canestriniidae.

(2) The order Phthiraptera

lice of the family Haematopinidae, lice of the family

Linognathidae, bird lice of the family Menoponidae, bird

lice of the family Philopteridae, and bird lice of the

family Trichodectidae.

(3) The order Siphonaptera

fleas of the family Pulicidae, for example,

Ctenocephalides canis and Ctenocephalides felis of

Ctenocephalides spp.; fleas of the family Tungidae, fleas of the family

Ceratophyllidae, and fleas of the family Leptopsyllidae.

(4) The order Hemiptera

(5) Insect pests of the order Diptera

mosquitos of the family Culicidae, black flies of the

family Simuliidae, biting midges of the family

Ceratopogonidae, horseflies of the family Tabanidae, flies

of the family Muscidae, tsetse flies of the family

Glossinidae, flesh flies of the family Sarcophagidae,

flies of the family Hippoboscidae, flies of the family

Calliphoridae, and flies of the family Oestridae.

[0130]

[Endoparasite control agent or expellant]

The endoparasite control agent or expellant of the

present invention contains at least one active ingredient

selected from the (hetero)aryl imidazole compounds of the

present invention. The amount of the (hetero)aryl

imidazole compound contained in the endoparasite control

agent or expellant of the present invention is not

particularly limited as long as its endoparasite control

effect is exhibited.

[0131]

The parasite targeted by the endoparasite control

agent or expellant of the present invention parasitizes

the inside of host animals, particularly, warm-blooded

animals or fishes (endoparasite). As the host animal for

which the endoparasite control agent or expellant of the

present invention is effective, a warm-blooded animal such

as a human and a livestock mammal (e.g., a cow, a horse, a

pig, sheep, and a goat), a laboratory animal (e.g., a mouse, a rat, and a sand rat), a pet animal (e.g., a hamster, a guinea pig, a dog, a cat, a horse, a squirrel, a rabbit, and a ferret), wild and zoo mammals (e.g., a monkey, a fox, a deer, and a buffalo), a fowl (e.g., a turkey, a duck, a chicken, a quail, and a goose), and a pet bird (e.g., a pigeon, a parrot, a myna bird, a Java sparrow, a parakeet, a Bengalese finch, and a canary bird); and fishes such as salmon, trout, and carp may be exemplified. Parasitic diseases mediated by parasites may be prevented or treated by controlling and expelling the parasites.

[0132]

As the parasite to be controlled or expelled, the

following may be exemplified.

(1) Nematodes of the order Dioctophymatida

(a) kidney worms of the family Dioctophymatidae, for

example, Dioctophyma renale of Dioctophyma spp.;

(b) kidney worms of the family Soboliphymatidae, for

example, Soboliphyme abei and Soboliphyme baturini of

Soboliphyme spp.

[0133]

(2) Nematodes of the order Trichocephalida

(a) trichinae of the family Trichinellidae, for example,

Trichinella spiralis of Trichinella spp.;

(b) whipworms of the family Trichuridae, for example,

Capillaria annulata, Capillaria contorta, Capillaria

hepatica, Capillaria perforans, Capillaria plica, and

Capillaria suis of Capillaria spp.; and Trichuris vulpis,

Trichuris discolor, Trichuris ovis, Trichuris skrjabini,

and Trichuris suis of Trichuris spp.

[0134]

(3) Nematodes of the order Rhabditida

threadworms of the family Strongyloididae, for example,

Strongyloides papillosus, Strongyloides planiceps,

Strongyloides ransomi, Strongyloides suis, Strongyloides

stercoralis, Strongyloides tumefaciens, and Strongyloides

ratti of Strongyloides spp.

[0135]

(4) Nematodes of the order Strongylida

hookworms of the family Ancylostomatidae, for example,

Ancylostoma braziliense, Ancylostoma caninum, Ancylostoma

duodenale, and Ancylostoma tubaeforme of Ancylostoma spp.;

Uncinaria stenocephala of Uncinaria spp.; and Bunostomum

phlebotomum and Bunostomum trigonocephalum of Bunostomum

spp.

[0136]

(5) Nematodes of the order Strongylida

(a) nematodes of the family Angiostrongylidae, for example,

Aelurostrongylus abstrusus of Aelurostrongylus spp.; and

Angiostrongylus vasorum and Angiostrongylus cantonesis of

Angiostrongylus spp.;

(b) nematodes of the family Crenosomatidae, for example,

Crenosoma aerophila and Crenosoma vulpis of Crenosoma

spp.; (c) nematodes of the family Filaroididae, for example,

Filaroides hirthi and Filaroides osleri of Filaroides

spp.; (d) lungworms of the family Metastrongylidae, for example,

Metastrongylus apri, Metastrongylus asymmetricus,

Metastrongylus pudendotectus, and Metastrongylus salmi of

Metastrongylus spp.;

(e) gapeworms of the family Syngamidae, for example,

Cyathostoma bronchialis of Cyathostoma spp.; and Syngamus

skrjabinomorpha and Syngamus trachea of Syngamus spp.

[0137]

(6) Nematodes of the order Strongylida

(a) nematodes of the family Molineidae, for example,

Nematodirus filicollis and Nematodirus spathiger of

Nematodirus spp.;

(b) nematodes of the family Dictyocaulidae, for example,

Dictyocaulus filaria and Dictyocaulus viviparus of

Dictyocaulus spp.;

(c) nematodes of the family Haemonchidae, for example,

Haemonchus contortus of Haemonchus spp.; and Mecistocirrus

digitatus of Mecistocirrus spp.;

(d) nematodes of the family Haemonchidae, for example,

Ostertagia ostertagi of Ostertagia spp.;

(e) nematodes of the family Heligmonellidae, for example,

Nippostrongylus braziliensis of Nippostrongylus spp.;

(f) nematodes of the family Trichostrongylidae, for

example, Trichostrongylus axei, Trichostrongylus

colubriformis, and Trichostrongylus tenuis of

Trichostrongylus spp.; Hyostrongylus rubidus of

Hyostrongylus spp.; and Obeliscoides cuniculi of

Obeliscoides spp.

[0138]

(7) Nematodes of the order Strongylida

(a) nematodes of the family Chabertiidae, for example,

Chabertia ovina of Chabertia spp.; and Oesophagostomum brevicaudatum, Oesophagostomum columbianum,

Oesophagostomum dentatum, Oesophagostonun georgianum,

Oesophagostonun naplestonei, Oesophagostonun

quadrispinulatun, Oesophagostonun radiatum,

Oesophagostomum venulosurn, and Oesophagostornum watanabei

of Oesophagostornurn spp.;

(b) nematodes of the family Stephanuridae, for example,

Stephanurus dentatus of Stephanurus spp.;

(c) nematodes of the family Strongylidae, for example,

Strongylus asini, Strongylus edentatus, Strongylus equinus,

and Strongylus vulgaris of Strongylus spp.

[0139]

(8) Nematodes of the order Oxyurida

nematodes of the family Oxyuridae, for example, Enterobius

anthropopitheci and Enterobius vermicularis of Enterobius

spp.; Oxyuris equi of Oxyuris spp.; and Passalurus

ambiguous of Passalurus spp.

[0140]

(9) Nematodes of the order Ascaridida

(a) nematodes of the family Ascaridiidae, for example,

Ascaridia galli of Ascaridia spp.;

(b) nematodes of the family Heterakidae, for example,

Heterakis beramporia, Heterakis brevispiculum, Heterakis

gallinarum, Heterakis pusilla, and Heterakis putaustralis

of Heterakis spp.;

(c) nematodes of the family Anisakidae, for example,

Anisakis simplex of Anisakis spp.;

(d) nematodes of the family Ascarididae, for example,

Ascaris lumbricoides and Ascaris suum of Ascaris spp.; and

Parascaris equorum of Parascaris spp.;

(e) nematodes of the family Toxocaridae, for example,

Toxocara canis, Toxocara leonina, Toxocara suum, Toxocara

vitulorum, and Toxocara cati of Toxocara spp.

[0141]

(10) Nematodes of the order Spirurida

(a) nematodes of the family Onchocercidae, for example,

Brugia malayi, Brugia pahangi, and Brugia patei of Brugia

spp.; Dipetalonema reconditum of Dipetalonema spp.; Dirofilaria immitis of Dirofilaria spp.; Filaria oculi of

Filaria spp.; and Onchocerca cervicalis, Onchocerca

gibsoni, and Onchocerca gutturosa of Onchocerca spp.;

(b) nematodes of the family Setariidae, for example,

Setaria digitata, Setaria equina, Setaria labiatopapillosa,

and Setaria marshalli of Setaria spp.; and Wuchereria

bancrofti of Wuchereria spp.;

(c) nematodes of the family Filariidae, for example,

Parafilaria multipapillosa of Parafilaria spp.; and

Stephanofilaria assamensis, Stephanofilaria dedoesi,

Stephanofilaria kaeli, Stephanofilaria okinawaensis, and

Stephanofilaria stilesi of Stephanofilaria spp.

[0142]

(11) Nematodes of the order Spirurida

(a) nematodes of the family Gnathostomatidae, for example,

Gnathostoma doloresi and Gnathostoma spinigerum of

Gnathostoma spp.;

(b) nematodes of the family Habronematidae, for example,

Habronema majus, Habronema microstoma, and Habronema

muscae of Habronema spp.; and Draschia megastoma of

Draschia spp.;

(c) nematodes of the family Physalopteridae, for example,

Physaloptera canis, Physaloptera cesticillata,

Physaloptera erdocyona, Physaloptera felidis, Physaloptera

gemina, Physaloptera papilloradiata, Physaloptera

praeputialis, Physaloptera pseudopraerutialis,

Physaloptera rara, Physaloptera sibirica, and Physaloptera

vulpineus of Physaloptera spp.;

(d) nematodes of the family Gongylonematidae, for example,

Gongylonema pulchrum of Gongylonema spp.;

(e) nematodes of the family Spirocercidae, for example,

Ascarops strongylina of Ascarops spp.;

(f) nematodes of the family Thelaziidae, for example,

Thelazia callipaeda, Thelazia gulosa, Thelazia lacrymalis,

Thelazia rhodesi, and Thelazia skrjabini of Thelazia spp.

[0143]

[Control agent for other pests]

The (hetero)aryl imidazole compound of the present

invention is additionally excellent in control effect on

insect pests that have a stinger or venom and harm humans

and animals, insect pests that mediate various pathogens

or disease-causing microbes, or insect pests that cause

discomfort to humans (toxic pests, hygienic pests, and

obnoxious pests, etc.).

[0144]

Specific examples thereof will be shown below.

(1) Insect pests of the order Hymenoptera

bees of the family Argidae, bees of the family Cynipidae,

bees of the family Diprionidae, ants of the family

Formicidae, bees of the family Mutillidae, and bees of the

family Vespidae.

[0145]

(2) Other insect pests

Blattodea, termites, Araneae, centipedes, millipedes,

crustacea, and Cimex lectularius.

[0146]

[Seed treatment agent or vegetative propagation organ

treatment agent]

The seed treatment agent or vegetative propagation

organ treatment agent of the present invention contains at

least one active ingredient selected from the (hetero)aryl

imidazole compounds of the present invention. The amount

of the (hetero)aryl imidazole compound contained in the

seed treatment agent or vegetative propagation organ

treatment agent of the present invention is not

particularly limited as long as its control effect is

exhibited.

[0147]

The vegetative propagation organ means a plant root,

stem, leaf, or the like having the ability to grow when

the site is separated from the body and placed in soil.

As the vegetative propagation organ, for example, a

tuberous root, a creeping root, a bulb, a corm or solid

bulb, a tuber, a rhizome, a stolon, a rhizophore, cane

cuttings, a propagule and a vine cutting are exemplified.

The stolon is also called runner. The propagule is also

called bulblet and is classified into a broad bud and a

bulbil. The vine cutting means a shoot (generic name for

leaves and stems) of sweet potato, Japanese yam, or the

like. The bulb, the corm or solid bulb, the tuber, the

rhizome, the cane cutting, the rhizophore and the tuberous root are also collectively called flower bulb. The cultivation of tubers and roots is started by planting tubers in soil. The tubers used are generally called seed tubers.

[0148]

The seed treatment agent or vegetative propagation

organ treatment agent of the present invention refers to a

preparation such as a wettable powder, wettable granules,

a flowable concentrate, or a dust formulated by mixing at

least one active ingredient selected from the (hetero)aryl

imidazole compounds of the present invention with an

appropriate solid carrier or liquid carrier, and, if

necessary, adding a surfactant or other formulation

adjuvants to the mixture. Also, the composition may

contain a binder. As the composition containing a binder,

a flowable concentrate (FS) for seed treatment is

exemplified.

[0149]

An adhesive substance that does not phytotoxically

affect plant seeds or vegetative propagation organs is

used as the binder. Specifically, at least one substance

selected from the group consisting of polyvinyl acetate,

polyvinyl alcohol, cellulose including ethylcellulose,

methylcellulose, hydroxymethylcellulose,

hydroxypropylcellulose, and carboxymethylcellulose,

polyvinylpyrrolidone, starch, modified starch, dextrin,

maltodextrin, polysaccharides including alginate and

chitosan, proteins including gelatin and casein, gum

arabic, shellac, calcium lignosulfonate, and a

methacrylamide monomer may be used.

[0150] Pests may be efficiently controlled by treating seed

tubers with at least one compound selected from the

(hetero)aryl imidazole compounds of the present invention.

As the method for treating a seed tuber with the

(hetero)aryl imidazole compound, dipping treatment, dust

coating treatment, coating treatment or the like is

exemplified. For the planting of seed tubers using a

tractor, the seed tubers may be treated by spraying a

chemical containing the (hetero)aryl imidazole compound

onto the seed tubers on the tractor.

[0151]

[Granular agrochemical composition for paddy rice seedling

nursery box treatment]

The granular agrochemical composition for paddy rice

seedling nursery box treatment (hereinafter, referred to

as the "granular agrochemical composition") of the present

invention contains at least one active ingredient selected

from the (hetero)aryl imidazole compounds of the present

invention. The amount of the (hetero)aryl imidazole

compound contained in the granular agrochemical

composition of the present invention is not particularly

limited as long as its control effect is exhibited.

[0152]

The granular agrochemical composition may be

obtained by various methods, but is obtained, for example,

by the extrusion granulation or the like of a powdery

composition combined one or more active ingredients with a

surfactant, a binder and an inorganic carrier, etc., if

necessary, by using a wet granulation method. More specifically, the active ingredient adjusted to a predetermined particle size was uniformly mixed with a necessary surfactant, binder and inorganic carrier. Then, an appropriate amount of water is added thereto, and the mixture is kneaded, shaped by extrusion through a screen having opened pores, and dried to prepare a granular agrochemical composition. The size of the pores used in this operation is usually preferably 0.5 mm to 1.5 mm.

[0153]

The particle size of the granular agrochemical

composition thus obtained is not particularly limited, but

is preferably 0.5 mm to 1.5 mm, and particularly

preferably 0.7 mm to 1.5 mm, in terms of average particle

size. The granules having such a particle size are

obtained by granulation, drying and subsequent sifting.

[0154]

In the granular agrochemical composition, if

necessary, a surfactant, a binder and an inorganic carrier

are combined. Among them, as the surfactant, for example,

a nonionic surfactant such as polyethylene glycol higher

fatty acid ester, polyoxyethylene alkyl ether,

polyoxyethylene alkyl aryl ether, polyoxyethylene aryl

phenyl ether, and sorbitan monoalkylate; an anionic

surfactant such as alkyl aryl sulfonate, dialkyl

sulfonate, alkyl sulfuric acid ester salt, alkyl

phosphoric acid ester salt, alkyl aryl sulfuric acid ester

salt, alkyl aryl phosphoric acid ester salt,

polyoxyethylene alkyl ether sulfuric acid ester salt,

naphthalenesulfonic acid salt and a condensate thereof,

ligninsulfonic acid salt, polycarboxylic acid-type polymer surfactant such as a copolymer of acrylic acid and itaconic acid or a copolymer of methacrylic acid and itaconic acid, a copolymer of maleic acid and styrene, a copolymer of maleic acid and diisobutylene and their alkali metal salts; polyoxyethylene aryl phenyl ether phosphoric acid ester salt; polyoxyethylene aryl phenyl ether sulfuric acid ester salt, or the like is exemplified.

The amount of this surfactant added is usually 0.1 parts

by weight to 5 parts by weight, though the amount is not

particularly limited.

[0155]

As the binder to be combined in the granular

agrochemical composition, for example,

carboxymethylcellulose metal salt, polyvinyl alcohol,

pregelatinized starch, dextrin, xanthan gum, guar seed gum,

sucrose, polyvinylpyrrolidone, polyacrylic acid metal salt

or the like is exemplified. The amount of the binder

combined is usually 0.1 parts by weight to 5 parts by

weight, though the amount is not particularly limited.

The inorganic carrier to be combined in the granules is

not particularly limited. For example, clays, calcium

carbonate, talc, diatomaceous earth, zeolite, attapulgite,

gypsum, porcelain stone or the like is exemplified.

[0156]

[Soil treatment agent]

The soil treatment according to the present

invention is, for example, a method of directly

controlling pests by applying an active ingredient to the

rhizospheres of plants to be protected from harm such as

eating by the pest, or controlling pests by penetrating and transporting an active ingredient to the inside of plant bodies from their roots or the like. Specifically, for example, planting hole treatment (planting hole spraying and planting hole soil-incorporation), plant foot treatment (plant foot spraying, plant foot soil incorporation, plant foot irrigation, and plant foot treatment at latter half of the seedling raising period), planting furrow treatment (planting furrow spraying and planting furrow soil-incorporation), planting row treatment (planting row spraying, planting row soil incorporation, and planting row spraying at the growing period), planting row treatment at sowing (planting row spraying at sowing and planting row soil-incorporation at sowing), broadcast treatment (broadcast soil spraying and broadcast soil-incorporation), band dressing, submerged treatment (broadcast submerged application and frame submerged application), other soil spraying treatments

(foliar granule spraying at the growing period, spraying

under tree crowns or around main stems, soil surface

spraying, soil surface incorporation, sowing hole spraying,

surface spraying on the ribbing ground, and inter-plant

spraying), other irrigation treatments (soil irrigation,

irrigation at the seedling raising period, chemical

injection treatment, irrigation on the plant foot,

chemical drip irrigation, and chemigation), seedling

nursery box treatment (seedling nursery box spraying,

seedling nursery box irrigation, and seedling nursery box

chemical flooding), seedling nursery tray treatment

(seedling nursery tray spraying, seedling nursery tray

irrigation, and flooded nursery tray spraying), nursery bed treatment (nursery bed spraying, nursery bed irrigation, flooded nursery bed spraying), seedling dipping, nursery soil-incorporation treatment (seedbed soil-incorporation and cover soil-incorporation), spraying before soil covering at sowing, spraying after soil covering at sowing, stem injection treatment, trunk injection treatment, trunk spraying treatment, and other treatments (plowing, surface soil-incorporation, soil incorporation into rain dropping lines, planting spot treatment, flower cluster granule spraying, and paste fertilizer mixing) are exemplified.

[0157]

[Bait agent]

The bait agent of the present invention contains at

least one active ingredient selected from the (hetero)aryl

imidazole compounds of the present invention. The amount

of the (hetero)aryl imidazole compound contained in the

bait agent of the present invention is not particularly

limited as long as its control effect is exhibited.

[0158]

The bait agent of the present invention may contain,

if necessary, an ingestibility improving component such as

a sugar, a carbohydrate, or a milk constituent, a

synergist, an aversive agent to prevent accidental

ingestion, a preservative, a flavor, an attractant, or the

like. The bait agent of the present invention may usually

be prepared by mixing the (hetero)aryl imidazole compound

with water and, if necessary, other components described

above. In the preparation of the bait agent of the

present invention, the (hetero)aryl imidazole compound may be the (hetero)aryl imidazole compound itself, or may be in the form of a formulation such as a dust, a wettable powder, a microcapsule, or a flowable concentrate.

[0159]

As the pest that may be effectively controlled with

the bait agent of the present invention, a cockroach such

as Periplaneta americana, Blattella germanica, and

Periplaneta fuliginosa, a click beetle such as Melanotus

okinawensis, an ant such as Monomorium intrudens and

Formica fusca, a deathwatch beetle such as Lasioderma

serricorne and Stegobium paniceum, a flour beetle such as

Tribolium castaneum and Tribolium confusum, a flat bark

beetle such as Oryzaephilus surinamensis and Cryptolestes

pusillus, a white ant such as Coptotermes formosanus and

Reticulitermes speratus, a fly such as Musca domestica,

Fannia canicularis, Phoridae, and Phlebotominae, and a

mosquito such as Culex pipiens, Aedes albopictus,

anopheles, and chironomids are exemplified.

[0160]

The bait agent of the present invention may be

applied as it is, or by impregnating a nonwoven fabric,

sponge, absorbent cotton, or the like, for example. This

aqueous bait agent or the nonwoven fabric, sponge,

absorbent cotton, or the like impregnated with the bait

agent is placed in a container such as a cup, a tray, or a

bottle, for example, and subjected to insect pest

expelling. In this respect, the apparatus for expelling

insect pest which is equipped with the container covered

outside and have some degree of space where insect pests

are capable of residing in order to ingest the bait agent of the present invention generally improves ingestibility and is thus effective.

[0161]

[Plant growth promoter]

The plant growth promoter of the present invention

contains at least one active ingredient selected from the

(hetero)aryl imidazole compounds of the present invention.

The amount of the (hetero)aryl imidazole compound

contained in the plant growth promoter of the present

invention is not particularly limited as long as its

effect of promoting plant growth is exhibited.

[0162]

In the plant growth promoter of the present

invention, if necessary, other components, a carrier, or

the like may be appropriately combined.

The (hetero)aryl imidazole compound of the present

invention may be used alone as a plant growth promoter,

but may usually be used as a formulation in a dosage form

such as a wettable powder, a liquid formulation, an oil

formulation, a dust, a granular formulation, or a

suspension concentrate (flowable) by mixing the

(hetero)aryl imidazole compound as an active ingredient

with common adjuvants for formulation use, such as a solid

carrier, a liquid carrier, a dispersant, a diluent, an

emulsifier, a spreading agent and a thickener.

[0163]

As the solid carrier or the liquid carrier, for

example, talc, clay, bentonite, kaolin, diatomaceous earth,

montmorillonite, mica, vermiculite, gypsum, calcium

carbonate, white carbon, wood flour, starch, alumina, silicate, glycopolymer, waxes, water, alcohols (methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, ethylene glycol, benzyl alcohol, etc.), a petroleum fraction (petroleum ether, kerosene, solvent naphtha, etc.), aliphatic or alicyclic hydrocarbons (n-hexane, cyclohexane, etc.), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, chlorobenzene, cumene, methylnaphthalene, etc.), halogenated hydrocarbons (chloroform, dichloromethane, etc.), ethers (isopropyl ether, ethylene oxide, tetrahydrofuran, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, methyl isobutyl ketone, etc.), esters (ethyl acetate, butyl acetate, ethylene glycol acetate, amyl acetate, etc.), acid amides (dimethylformamide, dimethylacetanilide, etc.), nitriles

(acetonitrile, propionitrile, acrylonitrile, etc.), sulfoxides (dimethyl sulfoxide, etc.), alcohol ethers (ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, etc.) or the like is exemplified.

[0164] As the adjuvant, for example, a nonionic surfactant (polyoxyethylene alkyl ether, polyoxyethylene alkyl ester, polyoxyethylene alkyl phenyl ether, polyoxyethylene

sorbitan alkyl ester, sorbitan alkyl ester, etc.), an anionic surfactant (alkyl benzenesulfonate, alkyl sulfosuccinate, polyoxyethylene alkyl sulfate, aryl sulfonate, etc.), a cationic surfactant (alkylamines,

polyoxyethylene alkylamines, quaternary ammonium salts, etc.), an amphoteric surfactant (alkylaminoethylglycine, alkyldimethylbetaine, etc.), polyvinyl alcohol, hydroxypropylcellulose, carboxymethylcellulose, gum arabic, tragacanth gum, xanthan gum, polyvinyl acetate, gelatin, casein, sodium alginate or the like is exemplified.

[0165]

As other components, other active ingredients such

as the fungicide, insecticide or acaricide, nematicide,

and pesticide for soil insect pests described above; a

plant regulating agent, a synergist, a fertilizer, a soil

improvement agent, animal feed or the like is exemplified.

The content of the (hetero)aryl imidazole compound

of the present invention in the plant growth promoter

differs variously depending on a preparation form, an

application method, and other conditions, but is

preferably 0.5 to 95% by weight, and particularly

preferably in the range of 2 to 70% by weight.

[0166]

The plant to which the plant growth promoter is to

be applied is not particularly limited. For example,

cereals of the family Poaceae, such as rice, barley, wheat,

Japanese millet, corn, and foxtail millet; vegetables such

as pumpkin, turnip, cabbage, daikon radish, Chinese

cabbage, spinach, bell pepper, and tomato; flowers and

ornamental plants such as chrysanthemum, gerbera, pansy,

orchid, peony, and tulip; beans such as azuki bean, kidney

bean, soybean, peanut, broad bean, and garden pea; tubers

and roots such as potato, sweet potato, eddo, Japanese yam,

and taro; Allium such as green onion, onion, and rakkyo,

or the like is exemplified.

[0167]

As for a method for applying the plant growth

promoter of the present invention, application to plants

(foliage application), application to plant growing soil

(soil application), application to paddy water (submerged

application), application to seeds (seed treatment), or

the like is possible.

[0168]

The applied amount of the plant growth promoter of

the present invention differs depending on a plant to

which the plant growth promoter is applied, etc., but is

in the range of 1 to 10000 ppm in terms of active

ingredient concentration and preferably 50 to 300 L/10 are

of a solution containing 10 to 1000 ppm of the active

ingredient, for foliage application, is preferably 0.1 to

1000 g/10 are and particularly preferably 10 to 100 g/10

are, of the active ingredient for soil application and

submerged application. Also, 0.001 to 50 g of the active

ingredient is preferably applied per kg of seeds for seed

treatment.

[0169]

[Formulation preparation]

Some formulation preparations of the pest control

agent, the insecticide or acaricide, the ectoparasite

control agent or the endoparasite control agent or

expellant of the present invention will be shown. However,

additives and addition ratios should not be limited by

these examples and may be changed in wide ranges. The

term "part" in the formulation preparations represents

part by weight.

[0170]

Hereinafter, the formulation preparations for

agriculture or horticulture and for paddy rice will be

shown.

[0171]

(Formulation 1: Wettable powder)

40 parts of the (hetero)aryl imidazole compound of

the present invention, 53 parts of diatomaceous earth, 4

parts of higher alcohol sulfuric acid ester, and 3 parts

of alkyl naphthalenesulfonate are uniformly mixed and

finely milled to obtain a wettable powder containing 40%

of the active ingredient.

[0172]

(Formulation 2: Emulsion)

30 parts of the (hetero)aryl imidazole compound of

the present invention, 33 parts of xylene, 30 parts of

dimethylformamide, and 7 parts of polyoxyethylene alkyl

allyl ether are mixed and dissolved to obtain an emulsion

containing 30% of the active ingredient.

[0173]

(Formulation 3: Granular formulation)

5 parts of the (hetero)aryl imidazole compound of

the present invention, 40 parts of talc, 38 parts of clay,

parts of bentonite, and 7 parts of sodium alkyl sulfate

are uniformly mixed, finely milled, and then granulated

into a granular shape of 0.5 to 1.0 mm in diameter to

obtain a granular formulation containing 5% of the active

ingredient.

[0174]

(Formulation 4: Granular formulation)

5 parts of the (hetero)aryl imidazole compound of

the present invention, 73 parts of clay, 20 parts of

bentonite, 1 part of dioctyl sulfosuccinate sodium salt,

and 1 part of potassium phosphate are well milled and

mixed, and after addition of water, the mixture is well

kneaded, then granulated, and dried to obtain a granular

formulation containing 5% of the active ingredient.

[0175]

(Formulation 5: Suspension)

10 parts of the (hetero)aryl imidazole compound of

the present invention, 4 parts of polyoxyethylene alkyl

allyl ether, 2 parts of polycarboxylic acid sodium salt,

parts of glycerin, 0.2 parts of xanthan gum, and 73.8

parts of water are mixed and wet-milled until the particle

size becomes 3 microns or smaller to obtain a suspension

containing 10% of the active ingredient.

[0176]

Hereinafter, the formulation preparations of the

ectoparasite control agent or the endoparasite control

agent or expellant will be shown.

[0177]

(Formulation 6: Granules)

5 parts of the (hetero)aryl imidazole compound of

the present invention are dissolved in an organic solvent

to obtain a solution. The solution is sprayed onto 94

parts of kaolin and 1 part of white carbon. Then, the

solvent is evaporated under reduced pressure. This type

of granules may be mixed with animal feed.

[0178]

(Formulation 7: Injectable filler)

0.1 to 1 parts of the (hetero)aryl imidazole

compound of the present invention and 99 to 99.9 parts of

peanut oil are uniformly mixed and then sterilized by

filtration through a sterilizing filter.

[0179]

(Formulation 8: Pore-on formulation)

5 parts of the (hetero)aryl imidazole compound of

the present invention, 10 parts of myristic acid ester,

and 85 parts of isopropanol are uniformly mixed to obtain

a pore-on formulation.

[0180]

(Formulation 9: Spot-on formulation)

10 to 15 parts of the (hetero)aryl imidazole

compound of the present invention, 10 parts of palmitic

acid ester, and 75 to 80 parts of isopropanol are

uniformly mixed to obtain a spot-on formulation.

[0181]

(Formulation 10: Spray formulation)

1 part of the (hetero)aryl imidazole compound of the

present invention, 10 parts of propylene glycol, and 89

parts of isopropanol are uniformly mixed to obtain a spray

formulation.

[0182]

Next, the present invention will be more

specifically described with reference to Examples of

compounds. However, the present invention is not limited

by the following Examples of compounds by any means.

[0183]

[Example 1]

Synthesis of 2-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1 yl)-l-methyl-1H-imidazol-2-yl)-5-cyclopropyl-3

(ethylsulfonyl)pyridine (compound No. d-2)

[0184]

(Step 1) Synthesis of 5-bromo-3-(ethylthio)picolinonitrile

02N EtSH NaH NC Br NC - / Br N -5CN 84% In a reaction vessel, 5-bromo-3-nitropicolinonitrile

(1 g) was dissolved in tetrahydrofuran (22 ml), and the

reaction vessel was replaced with nitrogen. Then, the

solution was cooled to -5°C and stirred. Ca. 60% sodium

hydride (0.2 g) was added thereto, and the mixture was

stirred at -5°C for 5 minutes. Then, ethylmercaptan (0.27

g) was added dropwise thereto, and the mixture was stirred

at -5°C for 30 minutes. The obtained solution was poured

into water, and extracted with ethyl acetate. The

obtained organic layer was washed with saturated brine,

dried over anhydrous magnesium sulfate, and filtered. The

filtrate was concentrated under reduced pressure. The

obtained concentrate was purified by silica gel column

chromatography to obtain 0.90 g of the title compound

(yield: 84%).

1H-NMR of the obtained title compound will be shown

below.

'H-NMR (CDCl 3 ) 5: 8.50 (1H, d), 7.83 (1H, d), 3.07 (2H, q),

1.41 (3H, t).

[0185]

(Step 2) Synthesis of 5-bromo-3

(ethylsulfonyl)picolinonitrile

F-/ N-S ,%mCPBA Q:bs NC Br NC-\ -Br N N CH2Ch N r.t. 99%

5-Bromo-3-(ethylthio)picolinonitrile (149 g) was dissolved in dichloromethane (1800 ml), and the solution was cooled to 00C and stirred. 70% m-chloroperbenzoic

acid (333 g) was added thereto, and the mixture was stirred overnight at room temperature. The obtained solution was poured into a mixed solution of a saturated aqueous solution of sodium bicarbonate and a saturated

aqueous solution of sodium thiosulfate, and extracted with dichloromethane. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated

under reduced pressure. The obtained concentrate was purified by silica gel column chromatography to obtain 167 g of the title compound (yield: 99%). 'H-NMR of the obtained title compound will be shown

below. 'H-NMR (CDCl 3 ) 5: 9.26 (lH, d), 8.72 (1H, d), 3.60 (2H, q), 1.23 (3H, t).

[0186]

(Step 3) Synthesis of 2-(5-bromo-3-(ethylsulfonyl)pyridin 2-yl)-l-methyl-lH-imidazole-5-carbaldehyde

0 i)NaOMe, MeOH, r.t 9/ ii) MeNH 2 .HCI, reflux 0-4

NC N / Br ji OHC Br

Br PrOH, TEA, reflux 46%

5-Bromo-3-(ethylsulfonyl)picolinonitrile (20 g) was

dissolved in methanol (220 ml). To the solution, a ca. 5

M solution of sodium methoxide in methanol (1.5 ml) was

added dropwise, and the mixture was stirred overnight at

room temperature. Methylamine hydrochloride (4.9 g) was

added thereto, and the mixture was heated and stirred for

2 hours under reflux. Triethylamine (30 ml) was added

thereto to obtain solution A.

Aside from this, 5-bromomalonaldehyde (16.5 g) and

isopropanol (220 ml) were mixed and stirred at 50°C for 1

hour to obtain solution B.

The solution B was added dropwise to the solution A,

and the mixture was heated and stirred for 4 hours under

reflux. The obtained solution was concentrated under

reduced pressure. The obtained residue was added to water,

and extracted with ethyl acetate. The obtained organic

layer was washed with saturated brine, dried over

anhydrous magnesium sulfate, and filtered. The filtrate

was concentrated under reduced pressure. The obtained

concentrate was purified by silica gel column

chromatography to obtain 12 g of the title compound

(yield: 46%).

1H-NMR of the obtained title compound will be shown

below.

1H-NMR (CDCl 3 ) 5: 9.86 (1H, s), 9.00 (1H, d), 8.62 (1H, d),

7.83 (1H, s), 3.89 (3H, s), 3.79 (2H, q), 1.36 (3H, t).

[0187]

(Step 4) Synthesis of 2-(5-cyclopropyl-3

(ethylsulfonyl)pyridin-2-yl)-1-methyl-1H-imidazole-5

carbaldehyde

>-BFaK Pd(OAc)2 O8 08K P(Cy)3 3 P0 4 O Br> XyleneN N OHC B H2 OHC 110°C 88%

In a reaction vessel, 2-(5-bromo-3

(ethylsulfonyl)pyridin-2-yl)-1-methyl-1H-imidazole-5

carbaldehyde (0.35 g) was dissolved in xylene (4.3 ml),

and the reaction vessel was replaced with argon. Then,

the solution was stirred at room temperature. Potassium

cyclopropyl trifluoroborate (0.36 g), palladium(II)

acetate (0.043 g), a solution of 20%

tricyclohexylphosphine in toluene (0.54 g), tripotassium

phosphate (0.82 g), and water (0.48 ml) were added thereto,

and the mixture was stirred at 1100C for 7 hours. The

obtained solution was poured into water, and extracted

with ethyl acetate. The obtained organic layer was washed

with saturated brine, dried over anhydrous magnesium

sulfate, and filtered. The filtrate was concentrated

under reduced pressure. The obtained concentrate was

purified by silica gel column chromatography to obtain

0.27 g of the title compound (yield: 88%).

1H-NMR of the obtained title compound will be shown

below.

1H-NMR (CDCl 3 ) 5: 9.84 (1H, s), 8.70 (1H, d), 8.02 (1H, d),

7.82 (1H, s), 3.84 (3H, s), 3.70 (2H, q), 2.12-2.06 (1H,

m), 1.31 (3H, t), 1.28-1.23 (2H, m), 0.95-0.91 (2H, m).

[0188]

(Step 5) Synthesis of 2-(5-(2-chloro-3,3,3-trifluoroprop

1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-5-cyclopropyl-3

(ethylsulfonyl)pyridine

N0='S ZnCC13CF 3 NAc,2O,CuCI CLI r N0OS

H N DMF 60C F 3C 0

In a reaction vessel, 2-(5-cyclopropyl-3

(ethylsulfonyl)pyridin-2-yl)-1-methyl-1H-imidazole-5

carbaldehyde (0.3 g) was dissolved in N,N

dimethylformamide (13 ml), and the solution was stirred at

room temperature. 1,1,1-Trichloro-2,2,2-trifluoroethane

(0.35 g), a zinc powder (0.31 g), acetic anhydride (0.14

g), and copper chloride (4.7 mg) were added thereto, and

the reaction vessel was replaced with argon, followed by

stirring overnight at 600C. The obtained solution was

poured to a 10% aqueous Rochelle salt solution, and

extracted with ethyl acetate. The obtained organic layer

was washed with saturated brine, dried over anhydrous

magnesium sulfate, and filtered. The filtrate was

concentrated under reduced pressure. The obtained

concentrate was purified by silica gel column

chromatography to obtain 0.23 g of the title compound (E/Z

= 17:83, yield: 59%).

1H-NMR and ' 9F-NMR of the obtained title compound

will be shown below.

'H-NMR(400 MHz, CDCl 3 ) (an E/Z mixture) 5: 8.68 (1H, d),

8.04 (1H, s), 8.02 (1H, d), 7.15 (1H, s), 3.74 (2H, q),

3.57 (3H, s), 2.12-2.06 (1H, m), 1.31 (3H, t), 1.28-1.20 9 (2H, m), 0.94-0.89 (2H, m); F-NMR(376 MHz, CDCl 3 -C 6 F 6 ): 5

-63.5(d) for the (E)-isomer and -68.4(s) for the (Z)

isomer.

[0189]

[Example 2]

Synthesis of 1-(6-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1

yl)-1-methyl-1H-imidazol-2-yl)-5-(ethylsulfonyl)pyridin-3

yl)cyclopropane-1-carbonitrile (compound No. d-15)

[0190]

(Step 1) Synthesis of 2-(5-(1,3-dioxolan-2-yl)-1-methyl

1H-imidazol-2-yl)-5-bromo-3-(ethylsulfonyl)pyridine

O=S Ethylene glycol OW N CN 20 -TsOH-H

Br Br OHCN N Toluene 0- N OHO reflux 96%

2-(5-Bromo-3-(ethylsulfonyl)pyridin-2-yl)-1-methyl

1H-imidazole-5-carbaldehyde (8.0 g) was dissolved in

toluene (150 ml), and the solution was stirred at room

temperature. Ethylene glycol (17 g) and p-toluenesulfonic

acid monohydrate (0.84 g) were added thereto, and the

mixture was heated and stirred overnight under reflux

using a Dean-Stark apparatus. The obtained solution was

poured into a saturated aqueous solution of sodium

bicarbonate, and extracted with chloroform. The obtained

organic layer was washed with saturated brine, dried over

anhydrous magnesium sulfate, and filtered. The filtrate

was concentrated under reduced pressure. The obtained concentrate was purified by silica gel column chromatography to obtain 8.5 g of the title compound

(yield: 96%).

'H-NMR of the obtained title compound will be shown

below.

'H-NMR (CDC13) 5: 8.94 (1H, d), 8.60 (1H, d), 7.19 (1H, s),

6.02 (1H, s), 4.17-4.00 (4H, m), 3.86 (2H, q), 3.64 (3H,

s), 1.33 (3H, t).

[0191]

(Step 2) Synthesis of 2-(6-(5-(1,3-dioxolan-2-yl)-1

methyl-1H-imidazol-2-yl)-5-(ethylsulfonyl)pyridin-3

yl)acetonitrile

O TMSCH2CN q./ o=s Pd2(dba) 3 O=S Br XantPhos O N CN \/ Br ZnF 2 I N DMF, 100°C \

In a reaction vessel, 2-(5-(1,3-dioxolan-2-yl)-1

methyl-1H-imidazol-2-yl)-5-bromo-3-(ethylsulfonyl)pyridine

(1.75 g) was dissolved in N,N-dimethylformamide (23 ml),

and the reaction vessel was replaced with argon. Then,

the solution was stirred at room temperature.

Trimethylsilylacetonitrile (0.98 g),

tris(dibenzylideneacetone)dipalladium(0) (0.40 g),

xantphos (0.50 g), and zinc fluoride (0.27 g) were added

thereto, and the mixture was stirred at 1000C for 3 hours.

The obtained solution was poured into a saturated aqueous

solution of ammonium chloride, and extracted with ethyl

acetate. The obtained organic layer was washed with

saturated brine, dried over anhydrous magnesium sulfate,

and filtered. The filtrate was concentrated under reduced pressure. The obtained concentrate was purified by silica gel column chromatography to obtain 0.51 g of the title compound (yield: 42%).

1H-NMR of the obtained title compound will be shown

below.

1H-NMR (CDCl 3 ) 5: 8.98-8.87 (1H, m), 8.46-8.39 (1H, m),

7.21 (1H, s), 6.03 (1H, s), 4.18-4.02 (4H, m), 3.96-3.93

(2H, m), 3.87 (2H, q), 3.65 (3H, s), 1.33 (3H, t).

[0192]

(Step 3) Synthesis of 1-(6-(5-(1,3-dioxolan-2-yl)-1

methyl-1H-imidazol-2-yl)-5-(ethylsulfonyl)pyridin-3

yl)cyclopropane-1-carbonitrile

=S Br=%r 0 N - CN B Br N DMFN/ N

Yo ~ 0°C to rt 0I_

2-(6-(5-(1,3-Dioxolan-2-yl)-1-methyl-lH-imidazol-2

yl)-5-(ethylsulfonyl)pyridin-3-yl)acetonitrile (0.50 g)

was dissolved in N,N-dimethylformamide (5 ml), and the

solution was stirred at 00C. Cesium carbonate (0.45 g)

was added thereto. Then, 1,2-dibromoethane (0.52 g) was

added dropwise thereto, and the mixture was stirred at 00C

for 20 minutes. Cesium carbonate (0.90 g) was added

thereto, and the mixture was stirred at room temperature

for 3 hours. The obtained solution was poured into water,

and extracted with ethyl acetate. The obtained organic

layer was washed with saturated brine, dried over

anhydrous magnesium sulfate, and filtered. The filtrate

was concentrated under reduced pressure. The obtained

concentrate was purified by silica gel column chromatography to obtain 0.29 g of the title compound

(yield: 54%).

1H-NMR of the obtained title compound will be shown

below.

'H-NMR (CDCl 3 ) 5: 8.97 (1H, d), 8.17 (1H, d), 7.19 (1H, s),

6.02 (1H, s), 4.18-4.01 (4H, m), 3.85 (2H, q), 3.64 (3H,

s), 1.97 (2H, dd), 1.61 (2H, dd), 1.31 (3H, t).

[0193]

(Step 4) Synthesis of 1-(5-(ethylsulfonyl)-6-(5-formyl-l

methyl-1H-imidazol-2-yl)pyridin-3-yl)cyclopropane-1

carbonitrile

N CIN 10% HCI aq. N - C

N N THFO to rt H N N

1-(6-(5-(1,3-Dioxolan-2-yl)-1-methyl-1H-imidazol-2

yl)-5-(ethylsulfonyl)pyridin-3-yl)cyclopropane-1

carbonitrile (0.24 g) was dissolved in tetrahydrofuran (10

ml), and the solution was stirred at 00C. 10%

hydrochloric acid (2 ml) was added thereto, and the

mixture was stirred at room temperature for 3 hours. The

obtained solution was poured into a saturated aqueous

solution of sodium bicarbonate, and extracted with ethyl

acetate. The obtained organic layer was washed with

saturated brine, dried over anhydrous magnesium sulfate,

and filtered. The filtrate was concentrated under reduced

pressure. The obtained concentrate was purified by silica

gel column chromatography to obtain 0.23 g of the title

compound (yield: 54%).

1H-NMR of the obtained title compound will be shown

below.

1H-NMR (CDCl 3 ) 5: 9.86 (1H, s), 9.00 (1H, d), 8.20 (1H, d),

7.83 (1H, s), 3.88 (3H, s), 3.79 (2H, dd), 2.01 (2H, dd),

1.64 (2H, dd), 1.34 (3H, t).

[0194]

(Step 5) Synthesis of 1-(6-(5-(2-chloro-3,3,3

trifluoroprop-1-en-1-yl)-l-methyl-1H-imidazol-2-yl)-5

(ethylsulfonyl)pyridin-3-yl)cyclopropane-1-carbonitrile

0=S Zn,CCI3CF3 0.=S C- IN Ao 2O.OCI0 -N CIN

H N DMF F N N 0

In a reaction vessel, 1-(5-(ethylsulfonyl)-6-(5

formyl-1-methyl-lH-imidazol-2-yl)pyridin-3

yl)cyclopropane-1-carbonitrile (0.23 g) was dissolved in

N,N-dimethylformamide (10 ml), and the solution was

stirred at room temperature. 1,1,1-Trichloro-2,2,2

trifluoroethane (3.1 g), a zinc powder (2.0 g), acetic

anhydride (1.0 g), and copper chloride (3.0 mg) were added

thereto, and the reaction vessel was replaced with argon,

followed by stirring overnight at 600C. The obtained

solution was poured to a saturated aqueous solution of

sodium bicarbonate, and extracted with ethyl acetate. The

obtained organic layer was washed with saturated brine,

dried over anhydrous magnesium sulfate, and filtered. The

filtrate was concentrated under reduced pressure. The

obtained concentrate was purified by silica gel column

chromatography to obtain 0.09 g of the title compound (E/Z

= 18:82, yield: 30%).

'H-NMR and ' 9F-NMR of the obtained title compound

will be shown below.

1H-NMR(400 MHz, CDCl 3 ) (an E/Z mixture) 5: 8.99 (1H, d),

8.19 (1H, d), 8.05 (1H, s), 7.16 (1H, s), 3.85 (2H, q),

3.63 (3H, s), 2.00 (2H, dd), 1.63 (2H, dd), 1.34 (3H, t);

19 F-NMR(376 MHz, CDCl 3 -C 6 F 6 ): 5 -63.5 (s) for the (E)-isomer

and -68.5 (s) for the (Z)-isomer.

[0195]

Some compounds of the present invention produced in

the same way as in Examples described above are shown in

Tables 1 and 2. Table 1 shows the substituents of the

compound represented by the formula (I). In the tables,

properties or melting point (m.p.) are also shown as the

physical properties of each compound.

In Table 1, Me represents a methyl group, Et

represents an ethyl group, °Pr represents a cyclopropyl

group, and cPen represents a cyclopentyl group.

[0196]

R1 _4

N B

R2 (1)

[019 7] __________________ ____Table 1 Compound xB1 R' R' R Configuration Physical properties No. d-1 5-Pr N S0 2Et Me CHGHGFOF, E Mi.. 142-143('C) d-2 5-'Pr N SO 2 Et Me CH=1CF 3 E/Z Mi.. 180-182('C) d-3 5-'Pr CH SOEt Me CH=OHOFCFCF, E m.p.:149-151(C) d-4 5-Pr 7N SO 2Et Me CH=CHOFOFCFCF, E M.P.: 110-112 (C) d-5 5-'Pr JOH SO 2 Et Me CI-IOHOFCF, E m..:154-156 (t) d-6 5-'Pr OH SlEt Me CH-lO(CD)CF3 E/Z viscous oil d-7 5-'Pr -- H SOEt Me 0O=(Cl)CF, 17 Mf.P.:170-172(oC) d-8 5s-Pr - N S02Et Me CH=00l2 - m.p. 159-161 (C) d-9 ;5-*Pr N S0 2Et Me CH=C(F)CF2CF3 Z M.P.: 122-124 (C) d-10 5-cPr N SO 2Et Me CH-lC(F)OFOF, E mip.:151-153(M) d-l I 5-'Pr N 502Et Me CH=OBrF E nip.: 148-150 (C) d-3 5-r d-12 5-'Pr N SOEt SO 2Et Me CH=OCOF 2CF, z nip.: 117-119 (C) Me OH=C(Cl)CF OF 2 2 OF, Z r.p ;103-105 (t) d-4 -Pr N SO2Et Me CH=C(Ul)G E m-p.:121-123 (C) d 5-01-CN-oPr) N SOEt Me CH=C(CI)CF, E/Z mp.5-() d-16 5-Cl-ON-Pr) N SO 2Et Me CH=CHCF2 E amorphous d-17 5-Cl -CCONH,2 HPr) N SO2Et Me CHCCCOOCF, E/Z m.P.: 205-207C 0M) d-18 5-C1-(CSNH,)-'Pr) N SOAE Me CH=OCCICF, E/Z mn.p.:215-217(t) d-9 5'rN S02Et Me OH=O(CF3)2 M.np.: 182-186(C) d-20 5-Cl-Me-'Pr) N SOEt Me CH=lC(CI)CF, E/Z m.P.: 13 7-139 (C) Id-21 5-0 -(pyridin-2-yi)-cPr) N SOzEt Me OWOC(CI)OF3 E/Z m-p.: 15 7-159 (C) d-22 5-(1-CN-'Pr) N 5 2Et Me CH=CHCFCF, E mn.p.: 158-160 (C) d-23 "-CN-Tr) N SO 2Et Ma CH=GHOFCF 2CFO 3 E M.p;140-142 (C) d-24 5-Pr N SOAE Me OHOC(Br)OF, E/Z M.P.: 166-168(tC) d-25 5-'Pr N SO 2Et Me CH=CHCF 2CFCF, E nip.: 143-145('C) d-26 5-Cl-Me-Pr) N S0 2Ft Me CH=CHCFCF, E m.p.: 94-97(C) d-27 5-'Pr N SOEt Me OH=CCF)OF,CFCF, Z mP.: 106-108(t) d-28 5-'Pr N SOM. Me CH=C(C)CF, E/Z M.P:z196-198(t) d-29 5-Cl-Me-'Pr) N SO 2Et Me CH=CHCFCFOF, M.P.:153-155(CO) d-30 5-'Pr N SOM. Me OI-IC(OI)OFCF, z M.P.: 151-153 (t) d-31 5-01-Me-'Pr) IN 5OAE Me CH=C(F)CFOF, Z M.p.: 119-121(C) d-32 5-Pen N SO2Et Me CH=OCCI)CF, E/Z m.1214t 1 d-33 5-Tr N SO2Et MeCH=IC(CI)CF3 m.P.: 159-161(C) d-34 5-'Pr N S5OEt Me CHO(O)0F, Z m.p.: 169-171(C) d-35 5-'Pr N OEt Me CFCC(F)OCFCF,CF 3 z M.P:1i13-115(tc)

d-36 5-Pr N__ SO 2Et Me CF=C(F)OCFCFCF, E nip.: 131-133(tC) d-37 _ I5-P_ _ _ _ N JOEt _ Me _ CF=O(F)OCF _ 3 ___2_ E/Z m.p.; 113-116(C)

[0198]

Table 2

Compound Structure Configuration Physical properties

NN

e-1 F N Z m.p.: 121-123 (C) F

N.

e-2 - N Z m.p. :190-192 (C) F F

e-3 N Z m.p.:244-246(C)

Fj,

c s0

e-4 c E/Z m.p.: 257-262 (°C)

0 S=0 F F CII

F F

[0199]

The H-NMR data of compounds having physical

properties of viscous oil or amorphous among the compounds

shown in Table 1 will be shown below.

Compound No. d-6: 1H-NMR(400 MHz, CDCl3): d 8.08 (s, 1H),

7.48 (s, 1H), 7.23 (d, 1H), 7.15 (d, 1H), 6.94 (dd, 1H),

3.47 (s, 3H), 3.42 (s, 3H), 2.79 (q, 2H), 1.98-1.90 (m,

1H), 1.22 (t, 3H), 1.21 (t, 3H), 1.07-1.02 (m, 2H), 0.78

0.84 (m, 2H).

Compound No. d-16: 1H-NMR(400 MHz, CDCl3): d 8.99 (d, 1H),

8.19 (d, 1H), 7.47 (s, 1H), 7.05-6.98 (m, 1H), 6.22-6.13

(m, 1H), 3.86 (q, 3H), 3.62 (s, 3H), 2.01-1.97 (m, 2H),

1.64-1.60 (m, 2H), 1.34 (t, 3H).

[0200]

[Biological test]

Test Examples given below show that the (hetero)aryl

imidazole compound of the present invention is useful as

an active ingredient for pest control agents and

ectoparasite control agents. The term "part" is based on

weight.

[0201]

(Preparation of test emulsion)

5 parts of the (hetero)aryl imidazole compound of

the present invention, 93.6 parts of dimethylformamide,

and 1.4 parts of polyoxyethylene alkyl aryl ether were

mixed and dissolved to prepare emulsion (I) containing 5%

of the active ingredient.

For a control, 98.5 parts of dimethylformamide and

1.5 parts of polyoxyethylene alkyl aryl ether were mixed

and dissolved to prepare emulsion (II).

[0202]

An insecticidal rate was calculated according to the

following expression:

Insecticidal rate (%) = (The number of dead insects

/ The number of tested insects) x 100

[0203]

(Test Example 1) Test of efficacy on Mythimna separata

0.8 g of commercially available artificial feed

(Insecta LFS, manufactured by Nosan Corp.) and 1 pl of the

emulsion (I) were well mixed to obtain test feed.

A plastic test container (capacity: 1.4 ml) was

packed with 0.2 g of the test feed per treatment plot.

Then, two second instar larvae of Mythimna separata were

inoculated to each treatment plot. A plastic lid was put

on the test container so as to prevent escape of the

second instar larvae of Mythimna separata. The container

was placed in a thermostat chamber of 250C. On the fifth

day, the insecticidal rate and the food intake were

examined. The test was conducted in duplicate.

[0204]

The insecticidal rate and the food intake of a

control plot were examined in the same way as in Test

Example 1 except that the emulsion (I) was changed to the

emulsion (II).

[0205]

Compounds of compound Nos. d-1, d-2, d-3, d-4, d-5,

d-6, d-7, d-8, d-1, d-12, d-13, d-14, d-15, d-16, d-18, d 19, d-20, d-21, d-22, d-23, d-24, d-27, d-28, d-29, d-30, d-32, d-33, d-34, d-35, d-36, d-37, e-1 and e-4 were

tested for their efficacy on Mythimna separata. All the

compounds had an insecticidal rate of 100% for Mythimna

separata or a food intake of 10% or less as compared with

the control plot. As is evident, the (hetero)aryl imidazole compound of the present invention is effective for Mythimna separata.

[0206]

(Test Example 2) Test of efficacy on Mythimna separata

The emulsion (I) was diluted with water such that

the concentration of the compound of the present invention

was 125 ppm. Corn leaves were dipped in the dilution for

seconds. The resulting corn leaves were placed in a

petri dish, and five second instar larvae of Mythimna

separata were released. The petri dish was placed in a

thermostat chamber having a temperature of 250C and a

humidity of 60%. Life and death were determined after 6

days from the release of the insects, and the insecticidal

rate was calculated. The test was conducted in duplicate.

[0207]

Compounds of compound Nos. d-1, d-2 and d-15 were

tested for their efficacy on Mythimna separata. All the

compounds exhibited an insecticidal rate of 80% or more

for Mythimna separata.

[0208]

(Test Example 3) Test of efficacy on Plutella xylostella

The emulsion (I) was diluted with water such that

the concentration of the compound of the present invention

was 125 ppm. Cabbage leaves were dipped in the dilution

for 30 seconds. The resulting cabbage leaves were placed

in a petri dish. Five second instar larvae of Plutella

xylostella were released thereto. The petri dish was

placed in a thermostat chamber having a temperature of

°C and a humidity of 60%. Life and death were

determined after 3 days from the release of the insects, and the insecticidal rate was calculated. The test was conducted in duplicate.

[0209]

Compounds of compound Nos. d-1, d-2, d-4, d-7, d-9,

d-10, d-12, d-13, d-15,d-18, d-20, d-21, d-22, d-23, d-24,

d-25, d-26, d-27, d-28, d-29, d-30, d-31, d-33 and d-34

were tested for their efficacy on Plutella xylostella.

All the compounds exhibited an insecticidal rate of 80% or

more for Plutella xylostella.

[0210]

(Test Example 4) Test of efficacy on Spodoptera litura

The emulsion (I) was diluted with water such that

the concentration of the compound of the present invention

was 125 ppm. Cabbage leaves were dipped in the dilution

for 30 seconds. The resulting cabbage leaves were placed

in a petri dish, and five second instar larvae of

Spodoptera litura were released. The petri dish was

placed in a thermostat chamber having a temperature of

°C and a humidity of 60%. Life and death were

determined after 6 days from the release of the insects,

and the insecticidal rate was calculated. The test was

conducted in duplicate.

[0211]

Compounds of compound Nos. d-2, d-12 and d-15 were

tested for their efficacy on Spodoptera litura. All the

compounds exhibited an insecticidal rate of 80% or more

for Spodoptera litura.

[0212]

(Test Example 5) Test of efficacy on Aphis craccivora

Seedlings of black-eyed peas were raised in 10-cm

pots. Aphis craccivora nymphs were inoculated onto

primary leaves. The emulsion (I) was diluted with water

such that the concentration of the compound of the present

invention was 125 ppm. The dilution was sprayed to the

black-eyed peas parasitized by the Aphis craccivora nymphs.

The black-eyed peas were placed in a thermostat chamber

having a temperature of 250C and a humidity of 60%. Life

and death of Aphis craccivora were determined after 4 days

from the spraying, and the insecticidal rate was

calculated. The test was conducted in duplicate.

[0213]

Compounds of compound Nos. d-1, d-2, d-3, d-4, d-5,

d-6, d-7, d-8, d-11, d-12, d-13, d-15, d-16, d-17, d-18, d-20, d-21, d-22, d-23, d-24, d-25, d-27, d-29, d-30, d-32,

d-34, d-35, d-36, d-37 and e-1 were tested for their

efficacy on Aphis craccivora. All the compounds exhibited

an insecticidal rate of 80% or more for Aphis craccivora.

[0214]

(Test Example 6) Test of efficacy on Phyllotreta striolata

The emulsion (I) was diluted with water such that

the concentration of the compound of the present invention

was 125 ppm to prepare a test chemical. The test chemical

was sprayed to Qing geng cai seedlings (at the seventh

true leaf stage) planted in 10-cm pots. The Qing geng cai

seedlings were dried in air and then placed in a plastic

cup. Ten Phyllotreta striolata adults were released

thereto. The plastic cup was stored in a thermostat

chamber having a temperature of 25°C and a humidity of 65%.

Life and death were determined after 7 days from the release of the insects, and the insecticidal rate was calculated. The test was conducted in duplicate.

[0215]

Compounds of compound Nos. d-1, d-2, d-4, d-9, d-10,

d-12, d-13, d-15, d-18, d-20, d-22, d-23, d-25, d-26, d-27,

d-29, d-31, d-33, d-34 and e-2 were tested for their

efficacy on Phyllotreta striolata adults. All the

compounds exhibited an insecticidal rate of 80% or more

for Phyllotreta striolata adults.

[0216]

(Test Example 7) Test of efficacy on Nilaparvata lugens

The emulsion (I) was diluted with water such that

the concentration of the compound of the present invention

was 125 ppm. Young seedlings of rice were dipped in the

dilution for 30 seconds. The young seedlings of rice were

dried in air and then placed in a plastic case. Five

second instar larvae of Nilaparvata lugens were released

thereto. The plastic case was stored in a thermostat

chamber having a temperature of 250C and a humidity of 65%.

Life and death were determined after 7 days from the

inoculation, and the insecticidal rate was calculated.

The test was conducted in duplicate.

[0217]

Compounds of compound Nos. d-1, d-2, d-9, d-13, d-15,

d-18, d-22, d-23, d-25, d-26, d-30 and d-31 were tested

for their efficacy on Nilaparvata lugens. All the

compounds exhibited an insecticidal rate of 80% or more

for Nilaparvata lugens.

[0218]

(Test Example 8) Test of efficacy on Musca domestica

The compound of the present invention was diluted

with acetone and the dilution was added dropwise at 100

ppm of the compounds of the present invention per g of a

cube of sugar. The cube of sugar was placed in a plastic

cup. Ten female adults of Musca domestica were released,

and a lid was put on the plastic cup. The plastic cup was

stored at 250C. Life and death were determined after 24

hours from the release of the insects, and the

insecticidal rate was calculated. The test was conducted

in duplicate.

[0219]

A compound of compound No. b-4 was tested for its

efficacy on Musca domestica. The compound exhibited an

insecticidal rate of 80% or more for Musca domestica.

[0220]

(Test Example 9) Test of efficacy on Aphis gossypii

Cucumber seedlings raised in 10-cm pots were pulled

out of the 10-cm pots. Soil attached to the root portions

was washed off with tap water, and the root portions were

dipped in tap water, followed by hydroponic culture.

Aphis gossypii nymphs were inoculated onto the cucumber

seedlings. The emulsion (I) was diluted with water such

that the concentration of the compound of the present

invention was 31 ppm to obtain a dilution. The tap water

was replaced with the dilution, and the hydroponic culture

was continued with the dilution in a thermostat chamber

having a temperature of 25°C and a humidity of 60%. Life

and death of Aphis gossypii were determined after 6 days

from the start of the hydroponic culture with the dilution, and the insecticidal rate was calculated. The test was conducted in duplicate.

[0221]

Compounds of compound Nos. d-1, d-2, d-9, d-15, d-18,

d-26, d-27 and d-33 were tested for their efficacy on

Aphis gossypii. All the compounds exhibited an

insecticidal rate of 80% or more for Aphis gossypii.

[0222]

(Test Example 10) Test of efficacy on Phyllotreta

striolata

The emulsion (I) was diluted with water such that

the concentration of the compound of the present invention

was 31 ppm to prepare a test chemical. The test chemical

was sprayed to Qing geng cai seedlings (at the seventh

true leaf stage) planted in 10-cm pots. The Qing geng cai

seedlings were dried in air and then placed in a plastic

cup. Ten Phyllotreta striolata adults were released

thereto. The plastic cup was stored in a thermostat

chamber having a temperature of 250C and a humidity of 65%.

Life and death were determined after 7 days from the

release of the insects, and the insecticidal rate was

calculated. The test was conducted in duplicate.

[0223]

Compounds of compound Nos. d-1, d-2, d-4, d-9, d-10,

d-12, d-13, d-15, d-18, d-20, d-22, d-23, d-25, d-26, d-27, d-29, d-33, d-34 and e-2 were tested for their efficacy on

Phyllotreta striolata adults. All the compounds exhibited

an insecticidal rate of 80% or more for Phyllotreta

striolata adults.

[0224]

All the compounds selected at random from among the

(hetero)aryl imidazole compounds of the present invention

exerted the effect as described above. It may therefore

be understood that the (hetero)aryl imidazole compound of

the present invention, including unillustrated compounds,

is a compound having an effect such as a pest control

effect, particularly, an acaricidal or insecticidal effect.

It may also be understood that the (hetero)aryl imidazole

compound of the present invention is a compound also

having an effect on parasites harmful to humans and

animals, such as ectoparasites.

Claims (12)

1. A compound represented by the formula (I), an N-oxide

compound, stereoisomer, tautomer or hydrate thereof or a

salt of any of these compounds:

R1 N -

N BI X R R2

wherein

B represents a nitrogen atom or CH;

X represents a substituted or unsubstituted C3-8

cycloalkyl group;

R represents a substituted or unsubstituted C1-6

alkylthio group or a substituted or unsubstituted C1-6

alkylsulfonyl group;

R2 represents a substituted or unsubstituted C1-6

alkyl group; and

R represents a substituted or unsubstituted C2-6

alkenyl group.

2. The compound according to claim 1, an N-oxide compound,

stereoisomer, tautomer or hydrate thereof or a salt of any

of these compounds, wherein the formula (I) is the formula

(II):

R' N4

R4 N N X

R3 (IT)

wherein R , R2 , and X have the same meanings as described in

the formula (I) ; R 3 represents a hydrogen atom or a halogeno group; R 4 represents a C1-4 haloalkyl group; and the carbon-carbon double stereo bond represents an E

form or a Z form, or a mixture thereof.

3. A compound represented by any one of the formula (III) to the formula (X), an N-oxide compound, stereoisomer,

tautomer or hydrate thereof or a salt of any of these compounds:

F FNI) F F N N F FV)

O=S N\N

F F (IV) 10 wherein the carbon-carbon double stereo bond represents an

E form or a Z form, or a mixture thereof;

F F N(V N FO F F. N

F F N N N F (V)

CF HI N F C N

ONNI N

F F (VX)

wherein the carbon-carbon double stereo bond represents an

E form or a Z form, or a mixture thereof;

NN

F

F N N N F) FF (IR)

10 FF N F r N N N F F(X)

0\0

4. A pest control agent comprising at least one compound

selected from the group consisting of a compound according

to any one of claims 1 to 3, an N-oxide compound,

stereoisomer, tautomer and hydrate thereof and a salt of

any of these compounds, as an active ingredient.

5. An insecticide or acaricide comprising at least one

compound selected from the group consisting of a compound

according to any one of claims 1 to 3, an N-oxide compound,

stereoisomer, tautomer and hydrate thereof and a salt of

any of these compounds, as an active ingredient.

6. An ectoparasite control agent comprising at least one

compound selected from the group consisting of a compound

according to any one of claims 1 to 3, an N-oxide compound,

stereoisomer, tautomer and hydrate thereof and a salt of

any of these compounds, as an active ingredient.

7. An endoparasite control agent or expellant comprising

at least one compound selected from the group consisting

of a compound according to any one of claims 1 to 3, an N

oxide compound, stereoisomer, tautomer and hydrate thereof

and a salt of any of these compounds, as an active

ingredient.

8. A seed treatment agent or vegetative propagation organ

treatment agent comprising at least one compound selected

from the group consisting of a compound according to any

one of claims 1 to 3, an N-oxide compound, stereoisomer, tautomer and hydrate thereof and a salt of any of these compounds, as an active ingredient.

9. A granular agrochemical composition for paddy rice

seedling nursery box treatment comprising at least one

compound selected from the group consisting of a compound

according to any one of claims 1 to 3, an N-oxide compound,

stereoisomer, tautomer and hydrate thereof and a salt of

any of these compounds, as an active ingredient.

10. A soil treatment agent comprising at least one

compound selected from the group consisting of a compound

according to any one of claims 1 to 3, an N-oxide compound,

stereoisomer, tautomer and hydrate thereof and a salt of

any of these compounds, as an active ingredient.

11. A bait agent comprising at least one compound selected

from the group consisting of a compound according to any

one of claims 1 to 3, an N-oxide compound, stereoisomer,

tautomer and hydrate thereof and a salt of any of these

compounds, as an active ingredient.

12. A plant growth promoter comprising at least one

compound selected from the group consisting of a compound

according to any one of claims 1 to 3, an N-oxide compound,

stereoisomer, tautomer and hydrate thereof and a salt of

any of these compounds, as an active ingredient.